Piperazine Dihydrochloride → Irbesartan

HRID 659754

反応式

HRID 659754 の反応式
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[C:8](=[O:25])[C:7]2([CH2:29][CH2:28][CH2:27][CH2:26]2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[N-:30]=[N+:31]=[N-:32].[Na+].Cl.Cl.N1CCNCC1>C1(C)C(C)=CC=CC=1>[CH3:4][CH2:3][CH2:2][CH2:1][C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:32]=[N:31][NH:30][N:24]=3)=[CH:13][CH:12]=2)[C:8](=[O:25])[C:7]2([CH2:26][CH2:27][CH2:28][CH2:29]2)[N:6]=1

参加物

5

反応物 3

HCID 8893Piperazine DihydrochlorideHCID 33557Sodium AzideHCID 98431164'-((2-Butyl-4-oxo-1,3-diazaspiro(4.4)non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrile

生成物 1

HCID 3749Irbesartan収率 96%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A mixture of 2-n-butyl-3-[(2′-cyanobiphenyl-4-yl)methyl]-1,3-diazaspiro-[4,4]-non-1-en-4-one (10 g), sodium azide (7.7 g) and piperazine dihydrochloride (7.5 g) in xylene (30 ml) was refluxed for 7 hours under stirring. The reaction was cooled to room temperature and extracted with 5% NaOH solution. The pooled alkaline solution was washed with toluene or xylene (15 ml) and the aqueous phase neutralized to pH 6.5 using concentrated HCL. The resulting suspension was stirred for 3 hours at room temperature and filtered obtain irbesartan (3.6 g, 96% purity by HPLC).

後処理

  1. temperaturewas refluxed for 7 hours
  2. extractionextracted with 5% NaOH solution
  3. washThe pooled alkaline solution was washed with toluene or xylene (15 ml)
  4. concentrationusing concentrated HCL
  5. stirringThe resulting suspension was stirred for 3 hours at room temperature
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-a67296b3abe540c4a17ddd7e7fd19fb6
出典データセット
uspto-grants-2011_12
特許番号
US08080670B2

関連ノート

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