Chloroacetonitrile → HCID 70594001, compound

HRID 1856576Notes

Reaction equation

HRID 1856576 reaction equation
[Cl:1][CH2:2][C:3]#[N:4].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[CH2:25][CH2:24]2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)C>[ClH:1].[ClH:1].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[NH:22][CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([O:37][CH2:2][C:3]#[N:4])=[CH:35][CH:36]=3)[CH2:27][CH2:28]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 155805Desmethylastemizole

Product 1

HCID 70594001HCID 70594001, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.2 parts of chloroacetonitrile, 6.7 parts of 4-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]phenol, 2.8 parts of potassium carbonate and 160 parts of 2-propanone is stirred and refluxed overnight. The reaction mixture is poured onto water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanone. The salt is filtered off and dried, yielding 7.4 parts (78.6%) of {4-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]phenoxy}acetonitrile dihydrochloride. monohydrate; mp. 224.6° C.

Workup

  1. temperaturerefluxed overnight
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted with methylbenzene
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt is filtered off
  8. customdried

Sources & evidence

ORD record
ord-c82842b894084c0a8b914da1d94e4722
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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