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

HRID 1765632

反応式

HRID 1765632 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b7c7d5c57fcf42109abf79a459c9fb32
出典データセット
uspto-grants-2007_06
特許番号
US07226929B2

関連ノート

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