Piperidine → 4-(Piperidine-1-carbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)oxycarbonylamino]-hexyl ester

HRID 260340노트

반응식

HRID 260340 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:14]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([O:46][C:47]([O:49]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:42][CH2:41]2)=[O:39])=[O:29])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[O:14]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([N:40]2[CH2:41][CH2:42][CH:43]([O:46][C:47]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:49])[CH2:44][CH2:45]2)=[O:39])=[O:29])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 152933074-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)-oxycarbonylamino]-hexyl ester

생성물 1

HCID 541283684-(Piperidine-1-carbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)oxycarbonylamino]-hexyl ester수율 101.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of piperidine (382 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. 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 1.85 g of an oil. Purification of the oil on silica gel (230-400 mesh) using 5%-20% ethyl acetate-methylene chloride as the eluent gave 1.23 g (68%) of the title compound as a white crystalline solid, mp 56°-61° C.

후처리

  1. additionAfter the addition the cooling bath
  2. customwas removed
  3. extractionThe reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-7cd6f0f027fd4a479ba799f121b2b9a1
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527804

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