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

HRID 979916노트

반응식

HRID 979916 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]#[N:31])[CH2:25][CH2:24]1.O.[OH-].[Na+]>O1CCCC1>[NH2:31][CH2:30][CH2:29][N:26]1[CH2:27][CH2:28][CH:23]([NH:22][C:14]2[N:13]([CH2:12][C:8]3[S:7][CH:11]=[CH:10][CH:9]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=2)[CH2:24][CH2:25]1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 135880204-[[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrileHCID 21226445Aluminium lithium hydride

생성물 1

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

시약·촉매·용매 1

HCID 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 ice bath and decomposed by the successive additions of 2.5 parts of water, 7.5 parts of 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. (131).

후처리

  1. temperatureat reflux
  2. temperatureThe reaction mixture was cooled in an ice 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-0c4284513f8145988e76efab7b7cc526
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04634704

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