Chloroacetonitrile → 4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidineacetonitrile

HRID 256668

Reaction equation

HRID 256668 reaction equation
Cl[CH2:2][C:3]#[N:4].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:21]([NH:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][CH:18]=3)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:21]([NH:22][CH:23]3[CH2:24][CH2:25][N:26]([CH2:2][C:3]#[N:4])[CH2:27][CH2:28]3)=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][CH:18]=3)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10340Sodium CarbonateHCID 197853439-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-9H-purin-8-amine

Product 1

HCID 197853404-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidineacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.22 parts of 2-chloroacetonitrile, 16 parts of 9-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-9H-purin-8-amine, 12.7 parts of sodium carbonate and 225 parts of N,N-dimethylformamide was stirred for 6 hours at room temperature. The reaction mixture was poured onto water. The product was extracted twice with trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was crystallized from acetonitrile. The precipitate was filtered off and the filtrate was evaporated, yielding 16 parts of 4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidineacetonitrile as a residue (compound 147).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionThe product was extracted twice with trichloromethane
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from acetonitrile
  7. filtrationThe precipitate was filtered off
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-11da556c18aa4377b1814d5a88123765
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Linked notes

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