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

HRID 979916Notes

Reaction equation

HRID 979916 reaction equation
[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

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 135880204-[[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0c4284513f8145988e76efab7b7cc526
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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