Ammonia → cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-(4-oxopentyl)4-piperidinyl]-2,2-dimethyl-7-benzofurancarboxamide hemihydrate

HRID 1492438노트

반응식

HRID 1492438 반응식
[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]3([CH3:30])OCC[O:26]3)[CH2:18][C@H:17]2[O:31][CH3:32])=[O:14])=[CH:4][C:3]=1[Cl:33].S(=O)(=O)(O)O.N>>[OH2:10].[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:11])([CH3:12])[O:10][C:6]=2[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25](=[O:26])[CH3:30])[CH2:18][C@H:17]2[O:31][CH3:32])=[O:14])=[CH:4][C:3]=1[Cl:33].[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:11])([CH3:12])[O:10][C:6]=2[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25](=[O:26])[CH3:30])[CH2:18][C@H:17]2[O:31][CH3:32])=[O:14])=[CH:4][C:3]=1[Cl:33]

참가 물질

4

반응물 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 67712855cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]-4-piperidinyl]2,2-dimethyl-7-benzofurancarboxamide

생성물 1

HCID 131718804cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-(4-oxopentyl)4-piperidinyl]-2,2-dimethyl-7-benzofurancarboxamide hemihydrate수율 51.6%

실험 절차

A mixture of 5.4 parts of cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]-4-piperidinyl]-2,2-dimethyl-7-benzofurancarboxamide and 85 ml of an aqueous sulfuric acid solution 1% was stirred for 2 hours at reflux temperature. After cooling, the reaction mixture was basified with ammonia and extracted with dichloromethane (2x). The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.4 parts (51.6%) of cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-(4-oxopentyl)-4-piperidinyl]-2,2-dimethyl-7-benzofurancarboxamide hemihydrate; mp. 137.7° C. (comp. 112).

후처리

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane (2x)
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5)
  8. customThe eluent of the desired fraction was evaporated
  9. filtrationThe product was filtered off
  10. customdried

출처 및 근거

ORD 기록
ord-ee157bf483e2473dbf2a51bd6f5fa16f
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05374637

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