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Chemistry
Heterocyclic Building Blocks
Piperidines
tert-Butyl 4-((((benzyloxy)carbonyl)amino)methyl)piperidine-1-carboxylate
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Piperidines
Aryls Amines Amides

[ CAS No. 155456-33-0 ] {[proInfo.proName]}

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Chemical Structure| 155456-33-0
Chemical Structure| 155456-33-0
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CAS No. :155456-33-0 MDL No. :MFCD09054712
Formula : C19H28N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 348.44 Pubchem ID :-
Synonyms :

Safety of [ 155456-33-0 ]

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Application In Synthesis of [ 155456-33-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 155456-33-0 ]

[ 155456-33-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 501-53-1 ]
  • [ 144222-22-0 ]
  • [ 155456-33-0 ]
YieldReaction ConditionsOperation in experiment
96% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; 1.5.113.A tert-Butyl 4-(aminomethyl)piperidine-l-carboxylate (0.611 g, 2.851 mmol) and diisopropylethylamine (0.479 g, 3.706 mmol) were dissolved in 30 mis of dry dichloromethane. To this mixture was added benzyl chloro formate (0.552 g, 3.136 mmol) and the mixture was stirred at room temperature for 2 hours. The mixture was then diluted with 50 mis of dichloromethane, washed once with IN aqueous HCl, one with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure to 950 mgs (96%) of the the title compound and used directly without further purification.
81% With dmap; triethylamine In dichloromethane at 20℃; for 16h; Cooling with ice; Inert atmosphere; 4.A Step A Compound 1-Boc-4-aminomethylpiperidine (1.00 g, 4.67 mmol) was dissolved in 50 mL of dichloromethane, triethylamine (2.36 g, 23.3 mmol), 4-dimethylaminopyridine (570 mg, 4.67 mmol), and CbzCl (2.39 g, 14.0 mmol) were added dropwise under an ice bath and nitrogen protection.Stir for 16 hours at room temperature.It was concentrated under reduced pressure, and the compound 1-Boc-4-(((benzyloxycarbonyl)amino)methyl)piperidine (1.32 g, yield 81%) was obtained by silica gel column chromatography
57% With pyridine In dichloromethane at 0 - 20℃; for 4h; 28 Benzyl chloroformate (10.53g, 61.7mmol) in DCM (3OmL) was added dropwise with stirring to an ice-cooled solution of 1 ,1 -dimethylethyl 4- (aminomethyl)-i-piperidinecarboxylate (12.Og, 56.1mmol) and pyridine (6.64g, 84.1 mmol) in DCM (8OmL). After the addition, the solution was stirred at 0- 5°C for 0.5h followed by 3.5h at room temperature. The reaction solution was then washed with 1 M HCI (3 x 3OmL) and brine (3OmL). It was then treated with decolourising charcoal and MgSO4, filtered and evaporated to dryness to leave a pale yellow oil. This was stirred and treated with EtOAc (2OmL), causing crystallisation of the product. Hexane (20OmL) was added and stirring was continued for 0.5h. The resulting solid was filtered and dried to afford 1 ,1- dimethylethyl 4-[([(phenylmethyl)oxy]carbonyl}amino)methyl]-1- piperidinecarboxylate (D28) as a white solid (11.15g, 57%). δH (CDCI3, 400MHz) 1.10 (2H, br.m), 1.45 (9H, s), 1.67 (3H, br.m), 2.68 (2H, br.m), 3.09 (2H, br.m), 4.10 (2H, br.m), 4.82 (1 H, br.m), 5.10 (2H, s) and 7.34 (5H, m).
With 4-methyl-morpholine In tetrahydrofuran at 5℃; for 2h; I.I.A.a 1-tert-Butyloxycarbonyl-4-(aminomethyl)piperidine (14 g; 65.33 mmol; prepared as described by Prugh et al., Synthetic Communications 22 (16), 2361-2365 (1992)) was dissolved in 50 ml of THF and, at 5° C., N-methylmorpholine (6.6 g) and benzyl chloroformate (12.6 g) were added, and the mixture was stirred for about 2 h. It was then concentrated, and the residue was taken up in CH2Cl2, washed with saturated NaCl solution, dried and filtered. The residue after concentration was 23.5 g of a yellow oil which was crystallized from methyl tert-butyl ether. 18 g; ESI-MS [M+H+]=293.15
With sodium carbonate In ethyl acetate 77.2 4-(Benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester Step 2 4-(Benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester To a solution of 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (21 g) in 100 mL of ethyl acetate cooled to 0° C. was added 100 mL of saturated sodium carbonate and benzyl chloroformate (17 g). The solution was stirred for 3 h, then separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum gave the product as an oil: 1H NMR (400 MHz, CDCl3): δ7.35 (m, 5H), 5.3 (d, 1H), 5.1 (s, 2H), 4.1 (br s, 2 H), 3.0 (br m, 2H), 2.6 (br m, 2H), 1.7 (m, 3H), 1.42 (s, 9H), 1.1 (m, 2H).
With sodium carbonate In ethyl acetate 174.2 4-(Benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester Step 2 4-(Benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester To a solution of 21 g of 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester in 100 mL of ethyl acetate cooled to 0° C. was added 100 mL of saturated sodium carbonate and 17 g of benzyl chloroformate. The solution was stirred for 3 h, then separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum gave the product as an oil: 1H NMR (400 MHz, CDCl3): 7.35 (m, 5H), 5.3 (d, 1H), 5.1 (s, 2H), 4.1 (br s, 2H), 3.0 (br m, 2H), 2.6 (br m, 2H), 1.7 (m, 3H), 1.42 (s, 9H), 1.1 (m, 2H).

Reference： [1]Current Patent Assignee: PFIZER INC; BRISTOL-MYERS SQUIBB CO - WO2011/22508, 2011, A2 Location in patent: Page/Page column 52; 53
[2]Current Patent Assignee: VIVAVISION BIOPHARMA TECH SHANGHAI - CN110724142, 2020, A Location in patent: Paragraph 0114; 0118-0120
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/68739, 2007, A1 Location in patent: Page/Page column 34-35
[4]Current Patent Assignee: ABBVIE INC - US7105508, 2006, B1 Location in patent: Page/Page column 68
[5]Current Patent Assignee: MERCK & CO INC - US2002/165241, 2002, A1
[6]Current Patent Assignee: MERCK & CO INC - US2003/119811, 2003, A1
  • 2
  • [ 155456-33-0 ]
  • [ 155456-34-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; Step 3 Piperidin-4-ylmethyl-carbamic acid benzyl ester A mixture of 35 g of 4-(benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester and 50 mL of 4N HCl in dioxane was stirred at rt for 3 h, then diluted with 200 mL of ether and filtered. The piperidin-4-ylmethyl-carbamic acid benzyl ester hydrochloride salt was obtained as a white fluffy solid. The free base was obtained by partitioning the hydrochloride between 50 mL chloroform and 50 mL saturated aqueous Na2CO3. MS (m+1)=249; 1H NMR (400 MHz, CDCl3)): 7.35 (m, 5H), 5.15 (s, 2H), 4.9 (br s, 1 H), 3.1 (m, 2H), 2.6 (m, 3H), 1.7 (m, 2H), 1.6 (m, 2H), 1.1 (m, 2H).
With hydrogenchloride; In 1,4-dioxane; Step 3 Piperidin-4-ylmethyl-carbamic acid benzyl ester A mixture of 4-(benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester (35 g) and 50 mL of 4N HCl in dioxane was stirred at room temperature for 3 h, then diluted with 200 mL of ether and filtered. There was obtained piperidin-4-ylmethyl-carbamic acid benzyl ester hydrochloride salt as a white fluffy solid. The free base was obtained by partitioning the hydrochloride between chloroform (50 mL) and saturated aqueous Na2CO3 (50 mL). 1H NMR (400 MHz, CDCl3)): delta7.35 (m, 5H), 5.15 (s, 2H), 4.9 (br s, 1 H), 3.1 (m, 2H), 2.6 (m, 3H), 1.7 (m, 2H), 1.6 (m, 2H), 1.1 (m, 2H). MS (m+1)=249.
Reference： [1]Patent: US2003/119811,2003,A1
[2]Patent: US2002/165241,2002,A1
  • 3
  • [ 155456-33-0 ]
  • [ 132431-09-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(Benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester With hydrogenchloride In 1,4-dioxane at 20℃; for 2.5h; Stage #2: With potassium carbonate In methanol; water; ethyl acetate for 2h; 29 1 , 1 -Dimethylethyl 4-[([(phenylmethyl)oxy]carbonyl}amino)methyl]-1 - piperidinecarboxylate (may be prepared as in Description 28) (11.1g, 31.9mmol) in dioxane (6OmL) was treated with 4M HCI in dioxane (12OmL) and the reaction mixture was stirred at room temperature for 2.5h. It was then evaporated to dryness and the resulting solid was further dried under vacuum overnight to afford phenylmethyl (4-piperidinylmethyl)carbamate as its HCI salt (9.21 g) slightly contaminated with residual dioxane. δH (DMSO d-6, 400MHz) 1.30 (2H1 m), 1.71 (3H, m), 2.81 (2H, m), 2.92 (2H, m), 5.01 (2H, s), 7.36 (5H, m), 8.65 (1 H, br. s) and 8.95 (1 H, br.s). A portion of this material (5.5Og, 19.3mmol) was suspended in EtOAc (15OmL) and MeOH (1OmL) and stirred vigorously with satd. K2CO3 solution (5OmL). After 1.5h water (3mL) was added and stirring continued for 0.5h. The two phases were separated and the aqueous phase was extracted with EtOAc (3OmL). The combined organic extracts were dried (MgSO4) and evaporated to leave a yellow oil which solidified on standing to afford the title compound as the free base (D29) (4.76g).
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/68739, 2007, A1 Location in patent: Page/Page column 35

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