Chloroacetonitrile → HCID 88501781, compound

HRID 845776Notes

Reaction equation

HRID 845776 reaction equation
Cl[CH2:2][C:3]#[N:4].Br.Br.Br.[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:19]([CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[N:16]=2)[CH2:10][CH2:9]1.C(=O)([O-])[O-:32].[Na+].[Na+]>CN(C)C=O>[OH2:32].[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][N:19]2[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[N:16]=[C:15]2[NH:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:2][C:3]#[N:4])[CH2:13][CH2:12]2)[CH:22]=1.[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][N:19]2[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[N:16]=[C:15]2[NH:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:2][C:3]#[N:4])[CH2:13][CH2:12]2)[CH:22]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10340Sodium CarbonateHCID 13588000HCID 13588000, compound

Product 1

HCID 88501781HCID 88501781, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.7 parts of 2-chloroacetonitrile, 19.5 parts of N-(4-piperidinyl)-1-(3-pyridinylmethyl)-1H-benzimidazol-2-amine trihydrobromide, 13 parts of sodium carbonate and 135 parts of N,N-dimethylformamide was stirred and heated for 3 hours at 50° C. The reaction mixture was poured onto water and extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile, yielding 6 parts (50%) of 4-[[1-(3-pyridinylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrile hemihydrate; mp. 204.5° C. (intermediate 73).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionextracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-1133490fb5a74fd8808d9dbff8e1120a
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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