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[ CAS No. 159874-38-1 ]

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2D
Chemical Structure| 159874-38-1
Chemical Structure| 159874-38-1
Structure of 159874-38-1 *Storage: {[proInfo.prStorage]}

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Product Details of [ 159874-38-1 ]

CAS No. :159874-38-1MDL No. :MFCD07772083
Formula : C15H22N2O2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :262.35Pubchem ID :23369962
Synonyms :

Computed Properties of [ 159874-38-1 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 159874-38-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362UN#:N/A
Hazard Statements:H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 159874-38-1 ]

  • Downstream synthetic route of [ 159874-38-1 ]

[ 159874-38-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 159874-38-1 ]
  • [ 895541-70-5 ]
YieldReaction ConditionsOperation in experiment
Method B; Preparation of ter/-butyl 4-{2-[ethyl(piperidin-4-yl)amino]-2-oxoethyl}piperazine-l- carboxylate.; Step 1: Preparation of tert-buty 4-{2-[{l-[(benzyloxy)carbonyl]piperidin-4-yl}(ethyl)amino]-2-oxoethyl}piperazine-l-carboxylate.; Diisopropylethylamine (1.3 ml) was added to a slurry of [4-(tert- butoxycarbonyl)piperazin-l-yl]acetic acid dihydrate (1.12g) [154478-71-6] in dichloromethane (16 ml) followed by HATU (1.82g) and the mixture was stirred under argon for 30 minutes. A solution of benzyl 4-(ethylarnino)piperidine-l-carboxylate (1.05g) [159874-38-1] in dichloromethane (4 ml) was added and the mixture was stirred for 24 hours, then diluted with dichloromethane (25 ml), washed consecutively with 2M NaOH (2x20 ml) and brine (1x20 ml) and dried. The solvent was evaporated and the residue was purified on a 4Og silica column eluted with a solvent gradient made up of ethyl acetate to 5% methanol: ethyl acetate. The yellow oil obtained was used directly in the next stage, LC-MS M+H 489 plus a HATU derived impurity M+H 175.1H NMR (CDCl3): 1.12 (3H, m), 1.44 (9H, s), 1.54-1.74 (8H, m), 2.48 (4H, d), 3.19-3.38 (4H, m), 3.44 (4H, d), 4.30 (IH, m), 5.14 (2H, s). 7.36 (5H, s).
  • 2
  • [ 159874-38-1 ]
  • [ 895541-71-6 ]
YieldReaction ConditionsOperation in experiment
Method C; Preparation of tert-butyl 4-{2-[ethyl(piperidin-4-yl)amino]-2-oxoethyl}piperidme-l- carboxylate.; Step 1 : Preparation of tert-butyl 4- {2-[ { 1 -[(benzyloxy)carbonyl]piperidin-4- yl} (ethyl)amino]-2-oxoethyl} piperidine- 1 -carboxylate.; l-Chloro-N,N-2-trimethylpropenylamine (891 mul) was added to a solution of [1- (tert-butoxycarbonyi)piperidm-4-yi]acetic acid (1.6Og) [157688-46-5] in dichloromethane (10 ml) and the mixture was stirred for 2 hours. An additional equivalent of l-chloro-N,N- 2-trimethylpropenylamine was added and stirring continued for 3 hours. A solution of benzyl 4-(ethylamino)piperidine-l -carboxylate (1.735g) and triethylamine (1.84 ml) in dichloromethane (30 ml) was added and the mixture was stirred for 16 hours then diluted with dichloromethane (30 ml) and washed with saturated ammonium chloride solution (2x25ml), 2M NaOH (2x25 ml) and brine (25 ml) and dried. Removal of the solvent gave an orange oil, LC-MS M+H (-Boc) 388. The material was used directly in step 2.
YieldReaction ConditionsOperation in experiment
b. 1-Benzyloxycarbonyl-4-(ethylamino)piperidine. Trifluoroacetic acid (108 mL) was added to a solution of the above piperidine (50.6 g) in dichlorometbane (200 mL) resulting in vigorous evolution of gas. After being stirred for 3 hours, the reaction mixture was evaporated, dissolved in dilute aqueous hydrochloric acid, and extracted with ethyl acetate (discarded). The acidic aqueous layer was basiliad with 1.0N sodium hydroxide until a pH of 10 was attained, and extracted with dichloromethane. The organic extracts were dried, evaporated, and distilled (178-179 C., 8.7 Pa) to give the title compound (30.0 g) as a colorless oil; MS: m/z=263(M+1); NMR (CD3 OD/CF3 COOH): 7.35 (m,5), 5.13 (s,2), 4.27 (m,2), 3.32 (m,1), 3.10 (q,2, J=7.3), 2.91 (m,2), 2.09 (m,2), 1.49 (m,2), 1.31 (t,3, J=7.3).
  • 4
  • [ 159874-38-1 ]
  • [ 624-83-9 ]
  • 1-benzyloxycarbonyl-4-(N-ethyl-N'-methylureido)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 18.a. 1-Benzyloxycarbonyl-4-(N-ethyl-N'-methylureido)piperidine. A solution of 1-benzyloxycarbonyl-4-(N-ethylamino)piperidine (4.0 g) and methyl isocyanate (11 mL) was stirred for 30 hours at ambient temperature. The reaction mixture was diluted with chloroform and evaporated to give the urea as an oil; MS: m/z=320(M+1). The material was used without further purification.
1-Benzyloxycarbonyl-4-(N-ethyl-N'-methylureido)piperidine. A solution of 1-benzyloxycarbonyl-4-(N-ethylamino)piperidine (4.0 g) and methyl isocyanate (11 mL) was stirred for 30 hours at ambient temperature. The reaction mixture was diluted with chloroform and evaporated to give the urea as an oil; MS: m/z=320(M+1). The material was used without further purification. Example 19.a.:
  • 5
  • [ 159874-38-1 ]
  • 1-Benzyloxycarbonyl-4-(N-ethyltrifluoroacetamido)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; trifluoroacetic anhydride; In dichloromethane; EXAMPLE 17.a. 1-Benzyloxycarbonyl-4-(N-ethyltrifluoroacetamido)piperidine. Trifluoroacetic anhydride (1.6 mL) was added to a solution of 1-benzyloxycarbonyl-4-(N-ethylamino)piperidine (2.0 g) and triethylamine (1.7 mL) in dichloromethane (40 mL). After being stirred for 3 hours, the reaction mixture was washed (1.0N hydrochloric acid, aqueous sodium bicarbonate, water), dried, and evaporated to give the amide (2.0 g) as an oil; MS: m/z=359(M+1); NMR (CDCl3 /CF3 COOH): ca. 1.3:1 mixture of rotamers, 7.36 (m,5), 5.18 (s,2), 4.35 (m,2), 4.20 (m,0.56), 3.98 (m,0.44), 3.50 (m,0.88), 3.42 (m,1.12), 2.93 (m,2), 1.83 (m,4), 1.29 (t,1.32, J=7.1), 1.21 (t,1.68, j=7.0).
With triethylamine; trifluoroacetic anhydride; In dichloromethane; 1-Benzyloxycarbonyl-4-(N-ethyltrifluoroacetamido)piperidine. Trifluoroacetic anhydride (1.6 mL) was added to a solution of 1-benzyloxycarbonyl-4-(N-ethylamino)piperidine (2.0 g) and triethylamine (1.7 mL) in dichloromethane (40 mL). After being stirred for 3 hours, the reaction mixture was washed (1.0 N hydrochloric acid, aqueous sodium bicarbonate, water), dried, and evaporated to give the amide (2.0 g) as an oil; MS: m/z=359(M+1); NMR (CDCl3 /CF3 COOH): ca. 1.3:1 mixture of rotamers, 7.36 (m,5), 5.18 (s,2), 4.35 (m,2), 4.20 (m,0.56), 3.98 (m,0.44), 3.50 (m,0.88), 3.42 (m,1.12), 2.93 (m,2), 1.83 (m,4), 1.29 (t,1.32, J=7.1), 1.21 (t,1.68, J=7.0). Example 18.a.:
  • 6
  • [ 159874-38-1 ]
  • benzyl 4-[ethyl(formyl)amino]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
toluene-4-sulfonic acid; In orthoformic acid triethyl ester; EXAMPLE 20.a. 1-Benzyloxycarbonyl-4-(N-ethylformamido)piperidine. A stirred solution of 1-benzyloxycarbonyl-4-(N-ethylamino)piperidine (1.5 g) in triethyl orthoformate (10 mL) containing a catalytic amount of p-toluenesulfonic acid was heated at 90 C. for 12 hours. The. reaction mixture was diluted with 1.0N hydrochloric acid (10 mL), stirred for 30 minutes, diluted with water, and extracted with dichloromethane. The organic extracts were washed (aqueous sodium bicarbonate, water), dried, and evaporated to an oil that slowly solidified. The solid was suspended in ether and filtered to give the formamido compound (1.0 g) as a white solid; MS: m/z=291(M+1); NMR: ca. 1.5:1 mixture of rotamers, 8.15 (s,0.6), 8.11 (s,0.4), 7.36 (m,5), 5.14 (m,2), 4.30 (m,2.4), 3.43 (m,0.6), 3.25 (m,2), 2.82 (m,2), 1.73 (m,4), 1.21 (t,1.2, J=7.2), 1.15 (t,l.8, J=7.1).
toluene-4-sulfonic acid; In orthoformic acid triethyl ester; 1-Benzyloxycarbonyl-4-(N-ethylformamido)piperidine. A stirred solution of 1-benzyloxycarbonyl-4-(N-ethylamino)piperidine (1.5 g) in triethyl orthoformate (10 mL) containing a catalytic amount of p-toluenesulfonic acid was heated at 90 C. for 12 hours. The reaction mixture was diluted with 1.0 N hydrochloric acid (10 mL), stirred for 30 minutes, diluted with water, and extracted with dichloromethane. The organic extracts were washed (aqueous sodium bicarbonate, water), dried, and evaporated to an oil that slowly solidified. The solid was suspended in ether and filtered to give the formamido compound (1.0 g) as a white solid; MS: m/z=291(M+1); NMR: ca. 1.5:1 mixture of rotamers, 8.15 (s,0.6), 8.11 (s,0.4), 7.36 (m,5), 5.14 (m,2), 4.30 (m,2.4), 3.43 (m,0.6), 3.25 (m,2), 2.82 (m,2), 1.73 (m,4), 1.21 (t,1.2, J=7.2), 1.15 (t,1.8, J=7.1).
  • 7
  • [ 159874-38-1 ]
  • 1-Benzyloxycarbonyl-4-(ethylpropionamido)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
c. 1-Benzyloxycarbonyl-4-(ethylpropionamido)piperidine. Using a procedure similar to that described in Example 10.a., except replacing 4-amino-1-benzyloxycarbonylpiperidine with 1-benzyloxycarbonyl-4-(N-ethylamino)piperidine and acetic anhydride with propionic anhydride, the title compound was obtained as an oil; MS: m/z=319(M+1); NMR: ca. 1.5:1 mixture of rotamers, 7.36 (m,5), 5.13 (m,2), 4.59 (m,0.58), 4.28 (m,2), 3.74 (m,0.42), 3.22 (m,2), 2.84 (m,2), 2.34 (m,2), 1.64 (m,4), 1.13 (m,6).
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