Sodium Hydroxide → 4-(3-(1-Methylethoxy)phenyl)-1-piperidinecarboxylic acid phenyl ester

HRID 397739ノート

反応式

HRID 397739 の反応式
C([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=2)[CH2:5][CH2:4]1)C.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:23]1([O:22][C:20]([N:3]2[CH2:8][CH2:7][CH:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=3)[CH2:5][CH2:4]2)=[O:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 23001057N-Ethyl-4-(3-(1-methylethoxy)phenyl)piperidine

生成物 1

HCID 537251114-(3-(1-Methylethoxy)phenyl)-1-piperidinecarboxylic acid phenyl ester収率 62%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
45 °C

実験手順

To N-ethyl-4-(3-(1-methylethoxy)phenyl)piperidine (Preparation 45, 2.0 g, 8.10 mmol) in toluene (20 ml) at 85° C. was added phenyl chloroformate (1.0 ml, 9.70 mmol) and the mixture was heated at reflux for 4 h. The solution was cooled to 45° C. and aqueous sodium hydroxide solution (1 ml of 50% aqueous sodium hydroxide solution in 8 ml of water) was added. The reaction mixture was cooled to room temperature and the organic layer was separated and washed with methanol: 1N aqueous hydrochloric acid (1:1, 2×20 ml), methanol: 1N aqueous sodium hydroxide solution (1:1, 25 ml) and water (20 ml). The organic extract was dried (MgSO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica column chromatography eluting with ethyl acetate:hexane (1:5) to give the title compound as an oil (1.7 g, 62%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe organic layer was separated
  5. washwashed with methanol
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give the crude product
  11. customThis was purified by silica column chromatography
  12. washeluting with ethyl acetate:hexane (1:5)

出典と根拠

ORDレコード
ord-55fc36ca6aa6455d98b4508a4be3a999
出典データセット
uspto-grants-2003_08
特許番号
US06610711B2

反応ノート

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