Potassium Carbonate → cis-4-[4-(4-Cyclobutylmethylpiperazin-1-yl)-3-(4,4-dimethylcyclohexyl)phenyl]-2,6-dimethylmorpholine

HRID 32180

반응식

HRID 32180 반응식
[CH3:1][C:2]1([CH3:28])[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[C:10]([N:20]3[CH2:25][C@H:24]([CH3:26])[O:23][C@H:22]([CH3:27])[CH2:21]3)[CH:11]=[CH:12][C:13]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:4][CH2:3]1.Br[CH2:30][CH:31]1[CH2:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C=O>[CH:31]1([CH2:30][N:17]2[CH2:16][CH2:15][N:14]([C:13]3[CH:12]=[CH:11][C:10]([N:20]4[CH2:25][C@H:24]([CH3:26])[O:23][C@H:22]([CH3:27])[CH2:21]4)=[CH:9][C:8]=3[CH:5]3[CH2:4][CH2:3][C:2]([CH3:28])([CH3:1])[CH2:7][CH2:6]3)[CH2:19][CH2:18]2)[CH2:34][CH2:33][CH2:32]1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2734658(Bromomethyl)cyclobutane2회HCID 59769447cis-4-[3-(4,4-Dimethylcyclohexyl)-4-piperazin-1-ylphenyl]-2,6-dimethylmorpholine

생성물 1

HCID 59769406cis-4-[4-(4-Cyclobutylmethylpiperazin-1-yl)-3-(4,4-dimethylcyclohexyl)phenyl]-2,6-dimethylmorpholine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of the cis-4-[3-(4,4-dimethylcyclohexyl)-4-piperazin-1-ylphenyl]-2,6-dimethylmorpholine (30 mg, 0.0778 mmol) produced in Example (61b), bromomethylcyclobutane (23 mg, 0.156 mmol), potassium carbonate (22 mg, 0.156 mmol) and dimethylformamide (1 mL) was stirred for 1 hour at an external temperature of 80° C. Then, bromomethylcyclobutane (23 mg, 0.156 mmol) was further added and stirring was continued for 2 hours under the same conditions. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was washed with water and brine in that order, and then the solvent was distilled off by nitrogen stream. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give cis-4-[4-(4-cyclobutylmethylpiperazin-1-yl)-3-(4,4-dimethylcyclohexyl)phenyl]-2,6-dimethylmorpholine as a colorless oil.

후처리

  1. stirringstirring
  2. waitwas continued for 2 hours under the same conditions
  3. washThe separated organic layer was washed with water and brine in that order
  4. distillationthe solvent was distilled off by nitrogen stream
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3f4e50d52dd443b886a52577dddca29c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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