Piperazine Dihydrochloride → Irbesartan

HRID 659754

반응식

HRID 659754 반응식
[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

참가 물질

5

반응물 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

생성물 1

HCID 3749Irbesartan수율 96%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a67296b3abe540c4a17ddd7e7fd19fb6
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080670B2

연결된 노트

불러오는 중…