Chloroacetonitrile → HCID 88501781, compound

HRID 637406Notes

Reaction equation

HRID 637406 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-6f5f85e81d224e82b1e48e0cf9fa6caa
Source dataset
uspto-grants-1985_12
Patent number
US04556660

Reaction notes

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