Chloroacetyl chloride → HCID 58371833, compound

HRID 1020929Notes

Reaction equation

HRID 1020929 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH:18]=3)=[CH:9][CH:8]=2)=[N:3]1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>ClCCl>[Cl:19][CH2:20][C:21]([N:16]1[CH2:15][CH:14]=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([C:4]3[N:5]=[CH:6][N:2]([CH3:1])[N:3]=3)=[CH:12][CH:11]=2)[CH2:18][CH2:17]1)=[O:22]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 58371904HCID 58371904, compound

Product 1

HCID 58371833HCID 58371833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 4-[4-(1-methyl-1H-[1,2,4]triazol-3-yl)-phenyl]-1,2,3,6-tetrahydro-pyridine 6BH (13.7 g, 44 mmol) in dichloromethane (450 ml) was added TEA (37 ml, 264 mmol) dropwise. After stirred at 0° C. for 10 min, chloroacetyl chloride (10.5 ml, 132 mmols) was added to the reaction mixture. The resulting mixture was stirred at 0° C. for 1 hr., and quenched with water (165 ml). The reaction mixture was diluted with dichloromethane (600 ml). The organic layer was separated and washed with brine, dried over MgSO4. Reaction mixture was concentrated to ˜50 ml, ether was added and the solid was filtered out to get the desired product 7BH (8.74 g).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 1 hr
  2. custom, and quenched with water (165 ml)
  3. additionThe reaction mixture was diluted with dichloromethane (600 ml)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customReaction mixture
  8. concentrationwas concentrated to ˜50 ml, ether
  9. additionwas added
  10. filtrationthe solid was filtered out

Sources & evidence

ORD record
ord-e1447efd56534e438032ed23af2d4f5a
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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