Sodium Hydroxide → N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-thienylmethyl)-1H-benzimidazol-2-amine

HRID 893671노트

반응식

HRID 893671 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.FC1C=CC(CNC2C=NC=CC=2[N+]([O-])=O)=CC=1.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[CH2:31][N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41][CH:42]1[CH2:47][CH2:46][N:45]([CH2:48][C:49]#[N:50])[CH2:44][CH2:43]1.[OH-].[Na+]>O1CCCC1.O>[NH2:50][CH2:49][CH2:48][N:45]1[CH2:46][CH2:47][CH:42]([NH:41][C:33]2[N:32]([CH2:31][C:27]3[S:26][CH:30]=[CH:29][CH:28]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[N:34]=2)[CH2:43][CH2:44]1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 135880204-[[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrileHCID 15614715HCID 15614715, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 13588045N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-thienylmethyl)-1H-benzimidazol-2-amine수율 72%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred mixture of 2.5 parts of lithium aluminum hydride and 225 parts of tetrahydrofuran was added dropwise a solution of 13 parts of 4-[[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrile in tetrahydrofuran under nitrogen atmosphere. Upon completion, stirring was continued for 3 hours at reflux. The reaction mixture was cooled in an ace bath and decomposed by the successive additions of 2.5 parts of water, 7.5 parts of a sodium hydroxide solution 15% and 7.5 parts of water. The whole was filtered over Hyflo and the filtrate was evaporated. The residue was crystallized from acetonitrile, yielding 9.5 parts (72%) of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-thienylmethyl)-1H-benzimidazol-2-amine; mp. 137.1° C. (intermediate 108).

후처리

  1. temperatureat reflux
  2. temperatureThe reaction mixture was cooled in an ace bath
  3. filtrationThe whole was filtered over Hyflo
  4. customthe filtrate was evaporated
  5. customThe residue was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-fb5c32c459c547429ef90546331a9c8f
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05126339

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