2-Bromopropane → 1-Isopropylpyridinium-4-carboxamide bromide

HRID 49855

反応式

HRID 49855 の反応式
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Br:10][CH:11]([CH3:13])[CH3:12]>CN(C=O)C>[Br-:10].[CH:11]([N+:5]1[CH:6]=[CH:7][C:2]([C:1]([NH2:9])=[O:8])=[CH:3][CH:4]=1)([CH3:13])[CH3:12]

参加物

4

反応物 2

HCID 63582-BromopropaneHCID 15074Isonicotinamide

生成物 1

HCID 234977611-Isopropylpyridinium-4-carboxamide bromide収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 200 mL of DMF, containing 50.0 g of isonicotinamide and 60 mL of 2-bromopropane, was refluxed 5.75 h. A white insoluble solid filtered from this cool solution gave 64.9 g (65%) of 1-isopropylpyridinium-4-carboxamide bromide, m/e=165, NMR. Catalytic reduction of this salt, with PtO2 in MeOH, gave 65.2 g (98%) of 1-isopropylpiperidine-4-carboxamide hydrobromide, m/e=171. An aqueous solution of this salt was basified, evaporated to dryness, and extracted with EtOAc to give 39.7 g (90%) of 1-isopropylpiperidine-4-carboxamide free base.

後処理

  1. temperaturewas refluxed 5.75 h
  2. filtrationA white insoluble solid filtered from this cool solution

出典と根拠

ORDレコード
ord-d2c726e0c19f44388fe48e216939a15c
出典データセット
uspto-grants-2004_03
特許番号
US06710057B2

関連ノート

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