Benzoic Acid → tert-Butyl 3-(benzoylamino)piperidine-1-carboxylate

HRID 1180973

반응식

HRID 1180973 반응식
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.[NH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1>CN(C=O)C.C(N(CC)CC)C>[C:1]([NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1)(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 5458091-BOC-3-AminopiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 22017033tert-Butyl 3-(benzoylamino)piperidine-1-carboxylate수율 39.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매

실험 절차

A solution of benzoic acid (0.123 g) in DMF (5 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.231 g), HOBT (0.163 g) and triethylamine (0.56 ml) and stirred at room temperature for 1 h. A solution of 3-amino-1-N-Boc-piperidine (0.3 g) in DMF (1 ml) was then added and stirring continued for 18 h. The solution was concentrated under reduced pressure to give an oil which was partitioned between ethyl acetate and water. The separated organic extracts were washed with water, hydrochloric acid (2N), saturated sodium bicarbonate solution and brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (0.120 g) as a yellow solid.

후처리

  1. stirringstirring
  2. waitcontinued for 18 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. customto give an oil which
  5. customwas partitioned between ethyl acetate and water
  6. washThe separated organic extracts were washed with water, hydrochloric acid (2N), saturated sodium bicarbonate solution and brine
  7. dry with materialdried (over magnesium sulphate)
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-db2281eb53c3413ab6f05803a40067d7
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282497B2

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