Benzoyl chloride → N-(4-benzyl-4-dimethylaminocyclohexyl)-N-propylbenzamide hydrochloride

HRID 1179035노트

반응식

HRID 1179035 반응식
[CH2:1]([C:8]1([N:18]([CH3:20])[CH3:19])[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:28]([Cl:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[OH-].[K+]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[ClH:36].[CH2:1]([C:8]1([N:18]([CH3:20])[CH3:19])[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][CH2:16][CH3:17])[C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 210989801-benzyl-N,N-dimethyl-N'-propylcyclohexane-1,4-diamine

생성물 1

HCID 69338285N-(4-benzyl-4-dimethylaminocyclohexyl)-N-propylbenzamide hydrochloride

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

700 mg of the nonpolar diastereomer of 1-benzyl-N,N-dimethyl-N′-propyl-cyclohexane-1,4-diamine were dissolved in 10 ml methylene chloride, and 370 μl triethylamine and approx. 10 mg DMAP (4-dimethylaminopyridine) were added. 311 μl benzoyl chloride were added dropwise, while cooling in an ice/methanol bath, and the reaction mixture was then stirred overnight, while warming to room temperature. For working up, 10 ml five molar KOH solution and 10 ml water were added, the mixture was stirred for ten minutes and extracted three times with 20 ml methylene chloride each time, the combined extracts were dried over magnesium sulfate and filtered and the filtrate was concentrated. From the crude product obtained (834 mg), 909 mg N-(4-benzyl-4-dimethylamino-cyclohexyl)-N-propyl-benzamide hydrochloride were prepared as described for example 1 with water and chlorotrimethylsilane in 2-butanone.

후처리

  1. temperaturewhile cooling in an ice/methanol bath
  2. stirringthe mixture was stirred for ten minutes
  3. extractionextracted three times with 20 ml methylene chloride each time
  4. dry with materialthe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-a2e120059db54a5a8a7c170f8420c055
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276518B2

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