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

HRID 893671ノート

反応式

HRID 893671 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fb5c32c459c547429ef90546331a9c8f
出典データセット
uspto-grants-1992_06
特許番号
US05126339

反応ノート

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