Benzyl Bromide → (3RS,4RS)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ol

HRID 1004942ノート

反応式

HRID 1004942 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[OH:14])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[CH2:21]([N:11]1[CH2:12][CH2:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]([OH:14])[CH2:10]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 221266524-(4-Fluorophenyl)piperidin-3-ol

生成物 1

HCID 22126857(3RS,4RS)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ol収率 74.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

A solution of 4.00 g (20.5 mmol) of (3RS,4RS)-4-(4-fluorophenyl)-piperidin-3-ol in 150 ml of ethanol was treated with 2.80 g (26.4 mmol) of sodium carbonate and refluxed. A solution of 2.50 ml (21.1 mmol) of benzyl bromide in 50 ml of ethanol was added dropwise within one hour and thereafter the mixture was held at reflux temperature for 2 hours. The pale brownish suspension was filtered and the filtrate was concentrated under reduced pressure. Subsequently, the residue was partitioned between methylene chloride and water, the organic phase was dried over magnesium sulphate and finally the solvent was distilled off under reduced pressure. The crude product was chromatographed on silica gel using a 2:3 mixture of ethyl acetate and hexane as the eluent. There were obtained 4.34 g (74% of theory) of (3RS,4RS)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ol as a colourless solid; MS: 285 (M)+.

後処理

  1. temperaturerefluxed
  2. temperatureat reflux temperature for 2 hours
  3. filtrationThe pale brownish suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customSubsequently, the residue was partitioned between methylene chloride and water
  6. dry with materialthe organic phase was dried over magnesium sulphate
  7. distillationfinally the solvent was distilled off under reduced pressure
  8. customThe crude product was chromatographed on silica gel using
  9. additiona 2:3 mixture of ethyl acetate and hexane as the eluent

出典と根拠

ORDレコード
ord-4275fdd12560453ba9814eadc4882da6
出典データセット
uspto-grants-2000_04
特許番号
US06051712

反応ノート

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