Dichloromethane → N-(2-[4-(Phenylmethyl)-1-piperazinyl]ethyl)tricyclo[3,3,1,13,7]-decane-1-carboxamide Dihydrochloride

HRID 1197838노트

반응식

HRID 1197838 반응식
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:14]1([CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][NH2:29])[CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C.[Cl:47]CCl>>[ClH:47].[ClH:47].[C:14]1([CH2:20][N:21]2[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][NH:29][C:11]([C:1]34[CH2:8][CH:7]5[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]5)[CH2:2]3)[CH2:10]4)=[O:13])[CH2:25][CH2:26]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 5

HCID 6344Dichloromethane3회HCID 8471TriethylamineHCID 132351-Adamantanecarboxylic acidHCID 76257Diethyl cyanophosphonateHCID 27353312-(4-Benzylpiperazin-1-yl)ethan-1-amine

생성물 1

HCID 45262462N-(2-[4-(Phenylmethyl)-1-piperazinyl]ethyl)tricyclo[3,3,1,13,7]-decane-1-carboxamide Dihydrochloride수율 10%

실험 절차

To a solution of adamantane-1-carboxylic acid (11.85 g, 0.065 mol) and 2-[4-(phenylmethyl)-1-piperazinyl]ethylamine (12.0 g, 0.054 mol) in dichloromethane (200 mL) at 4° C. was added, with stirring, a solution of diethylcyanophosphonate (11.8 mL, 0.065 mol) in dichloromethane (50 mL), followed by a solution of triethylamine (9.2 mL, 0.065 mol) in dichloromethane (50 mL). The resulting mixture was stirred overnight, during which time it came up to room temperature. The reaction mixture was then washed with 10% aqueous potassium carbonate (200 mL), dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The desired product (TLC on silica gel using 10% methanol/ethyl acetate, Rf=0.33) was isolated by crystallization from hexane and recrystallized from hexane. It was then converted to its dihydrochloride salt with isopropanolic HCl (12.71 g, 52%), mp=259°-260° C.

후처리

  1. stirringThe resulting mixture was stirred overnight, during which time it
  2. customcame up to room temperature
  3. washThe reaction mixture was then washed with 10% aqueous potassium carbonate (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated on a rotary evaporator

출처 및 근거

ORD 기록
ord-d8ad2b16c6fa47ad9b6fff6a941deebb
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278160

반응 노트

불러오는 중…