Triethylamine → 4-(4-Phenyl-butyl-carbamoyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)-oxycarbonylamino]-hexyl ester

HRID 260339

반응식

HRID 260339 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:19]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43]([N:45]2[CH2:50][CH2:49][CH:48]([O:51][C:52](OC3C=CC([N+]([O-])=O)=CC=3)=[O:53])[CH2:47][CH2:46]2)=[O:44])=[O:34])=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[O:19]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43]([N:45]2[CH2:50][CH2:49][CH:48]([O:51][C:52](=[O:53])[NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:47][CH2:46]2)=[O:44])=[O:34])=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 83242Benzenebutanamine2회HCID 15293307HCID 15293307, 화합물

생성물 1

HCID 98307104-(4-Phenyl-butyl-carbamoyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)-oxycarbonylamino]-hexyl ester수율 99.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4-phenylbutylamine (610 μl, 3.86 mmol) and triethylamine (2.24 mL, 16.1 mmol) in 30 mL of methylene chloride was added under nitrogen dropwise to a solution of the carbonate prepared in Example 5 (2.0 g, 3.22 mmol) in 30 mL of methylene chloride at ice bath temperature. After the addition the cooling bath was removed and the reaction stirred at room temperature overnight. An additional 204 μl (1.29 mmol) of 4-phenylbutylamine and 180 μl (1.29 mmol) of triethylamine were added and the reaction stirred at room temperature for approximately 7 hours. The reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 2.02 g of a crystalline solid. Purification of the solid on silica gel (230-400 mesh) using 5%-20% ethyl acetate-methylene chloride as the eluent gave 1.43 g (70%) of the title compounds as a white crystalline solid, mp 84°-86° C.

후처리

  1. additionAfter the addition the cooling bath
  2. customwas removed
  3. stirringthe reaction stirred at room temperature for approximately 7 hours
  4. extractionThe reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-7c5876b7c39e4ce98d87d26b58205a66
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527804

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