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[ CAS No. 1440-60-4 ]

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2D
Chemical Structure| 1440-60-4
Chemical Structure| 1440-60-4
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Product Details of [ 1440-60-4 ]

CAS No. :1440-60-4MDL No. :MFCD01095825
Formula : C7H12ClNO Boiling Point : 270.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :161.63Pubchem ID :222312
Synonyms :

Computed Properties of [ 1440-60-4 ]

TPSA : 20.3 H-Bond Acceptor Count : 1
XLogP3 : 1.2 H-Bond Donor Count : 0
SP3 : 0.86 Rotatable Bond Count : 1

Safety of [ 1440-60-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1440-60-4 ]

  • Upstream synthesis route of [ 1440-60-4 ]
  • Downstream synthetic route of [ 1440-60-4 ]

[ 1440-60-4 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
98% With triethylamine In dichloromethane at 0 - 20℃; for 6 h; General procedure: To a solution of morpholine (14a; 4.50 mL, 51.45 mmol) and triethylamine (7.90 mL, 56.68 mmol) in CH2Cl2 (80 mL) was slowly added 2-chloroacetyl chloride (6a; 3.70 mL, 46.45 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 6 h, and then diluted with CH2Cl2, washed with saturated NaHCO3 and brine, dried over MgSO4 and filtered. The residue was concentrated under reduced pressure to afford -chloroamide 15aa (7.55 g, 99percent) as a light yellow liquid
90% at 0 - 23℃; for 1 h; Inert atmosphere To a solution of piperidine (51.9 ml, 525 mmol, 2.1 equiv) in THF (1000 mL) was added chloroacetic chloride (19.9 ml, 250 mmol, 1.0 equiv) slowly at 0 °C under nitrogen atmosphere. The reaction was allowed to warm to 23 °C, and stirred for 1 hour. The reaction mixture was extracted with EA (2 x 500 ml) from sat. NH4C1 solution, the combined organic layer was washed by brine (300 mL), dried over anhydrous Na2S04. After filtration and evaporation under reduced pressure, the crude product (36.4g, 90percent) obtained was used directly for the next step without further purification. NMR (CDC13, 400 MHz, 25 °C) δ 4.06 (s, 2H), 3.54 (t, 7= 5.5 Hz, 2H), 3.43 (t, J= 5.2 Hz, 2H), 1.70-1.60 (m, 4H), 1.60-1.51 (m, 2H) ppm. 13C NMR (CDCb, 100 MHz, 25 °C) 164.9, 47.5, 43.4, 41.3, 26.4, 25.5, 24.4 ppm.
82% With pyridine In dichloromethane for 1 h; General procedure: To a stirred solution of the amine (2 g) in dichloromethane was added pyridine (1.2 eq.) followed by dropwise addition of the acid chloride(1.2 eq.). After 1 hr, further dichloromethane (10 ml) was added, the solution then washed successively with saturated aqueous sodium hydrogen carbonate, hydrochloric acid (2 M), water, then dried and the solvent removed under reduced pressure to give the amide.
70% With sodium hydrogencarbonate In dichloromethane at 0℃; for 1 h; General procedure: Propionyl chloride (6.0mmol) in dry CH2Cl2 (10mL) was added dropwise to a mixture of 4-methoxybenzenamine (5.0mmol), sodium bicarbonate (12.5mmol) and dry CH2Cl2 (15mL). The mixture was stirred in ice water bath for 1h and poured into water and then extracted with CH2Cl2 (3×30mL). The combined organic layer was washed with brine and dried over anhydrous MgSO4. The solvent was evaporated to dryness to afford the compound 4a. Others amide derivatives 4b–4s were synthesized similarly. Physical constants and spectral data of compounds 4a–4s are summarized below.
507 mg at 0 - 20℃; for 15 h; Piperidine (452.4 mg, 5.313 mmol) was dissolved in THF 2.5 ml. After a 2chloroacetylchloride (300 mg, 2.656 mmol) wasdissolved in 2.5 ml THF was added dropwise at 0 ° C for 5 minutes and stirred at room temperature for 15 hours. It was thendiluted with EA and washed three times with water. The organic layer was dehydrated with Na2SO4, and concentrated underreduced pressure to afford 507 mg of a yellow liquid. Obtained 2chloro1(piperidin1yl)ethanone154 mg (0.954 mmol),Preparation Example 2.3. The compound (250 mg, 0.795 mmol) and K2CO3 (439.7 mg, 3.181 mmol) obtained from wasdissolved in DMF 2.7 ml. 60 To stirred for 2 hours at 65 ° C. To cool to room temperature then diluted with EA and washed three times with water. The organic layer was dehydrated with Na2SO4, and concentrated under reduced pressure and thenseparated by column chromatography to give 297 mg of the title compound as a white solid.
12.7 g at 20℃; for 1 h; Piperidine 17 g, 60 ml of toluene were mixed under stirring to 18 g of chloroacetyl chloride and 120 ml of toluenedropwise addition, the reaction one hour at room temperature, the solid was filtered off, the filtrate was concentrated to dryness to give a pale yellow oil of 2-chloro -N - piperidyl acetamide 12.7 g.
507 mg at 0 - 20℃; for 15.0833 h; To a solution of piperidine(452.4 mg, 5.313 mmol)in THF(2.5 ml) was added dropwise a solution of 2-chloroacetyl chloride(300 mg, 2.656 mmol) in THF(2.5 ml) over 5 mm at 0. After stirring for 15 h at rt, the mixture was diluted with EtOAc and washed with water for three times. The organic layer was dried over Na2SO4 and concerntrated under reduced pressure to afford the desired product(507 mg) as a yellow liquid. A mixure of the yellow liquid, 2-chloro- 1 -(piperidin- 1 -yl)ethanone(432 mg, 2.67 mmol), tert-butyl 4-(2,6-difluoro-4-hydroxyphenyl)piperazine- 1 -carboxylate(700 mg, 2.227 mmol) and K2C03(769 mg, 5.567 mmol)in DMF(7.4 ml) was heated to 60 to 65 for 2 h. The mixture was allowed to cool down to ii, diluted with EtOAc and washed with water for three times. The organic layer was dried over Na2SO4, concentrated under reduced pressure. The residue was purified by column chromatography to afford the desired product(823 mg) as a white solid.LC-MS (ESI, mlz) = 440.2(M+H÷).
240 mg With triethylamine In dichloromethane In Step 1, 1 gram of Compound 35 was dissolved in DCM and then subjected to BBr3 to afford 930 milligrams of Compound 52. The H-NMR was clean. In Step 2, Compound 52 was reacted with sodium hydride and benzyl bromide to afford Compound 53. In Step 3, 200 milligrams of Compound 33 was dissolved in DCM and triethylamine and reacted with 2-chloroacetyl chloride to afford 240 milligrams of Compound 54 after work-up and purification. In Step 4 Compound 54 was then dissolved in DMF and reacted with sodium hydride and 4-(benzyloxy)phenol to afford 300 milligrams of Compound 55 after work-up and purification. In Step 5, 300 milligrams of Compound 55 was reduced by lithium aluminum hydride to afford 260 milligrams of Compound 56 as an oil after work-up and purification. The H-NMR was clean. In Step 6, 260 milligrams of Compound 56 was hydrogenated to afford 200 milligrams of Compound 57. The H-NMR was clean. In Step 8, 100 milligrams of Compound 57 was mixed with Compound 53 in DMF in the presence of cesium carbonate to afford 160 milligrams of Compound 58. In Step 10, 30 milligrams of Compound 58 was hydrogenated with palladium on carbon in the presence of hydrogen gas to afford 20 milligrams of Compound 106 after work-up and purification.

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