Sodium borohydride → HCID 53857745, compound

HRID 866503Notes

Reaction equation

HRID 866503 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]2[N:21]([CH3:22])[N:20]=[CH:19][C:18]=2[CH2:23][N:24]([CH3:26])[CH3:25])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:8].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]2[N:21]([CH3:22])[N:20]=[CH:19][C:18]=2[CH2:23][N:24]([CH3:26])[CH3:25])=[C:6]([CH:7]([OH:8])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20321593HCID 20321593, compound

Product 1

HCID 53857745HCID 53857745, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of 1.86 g of 5-chloro-2-(1-methyl-4-dimethylaminomethyl-5-pyrazolyl)-2'-fluorobenzophenone in 100 ml of ethanol is stirred for 21/2 hours at room temperature with 500 mg sodium borohydride. It is evaporated under reduced pressure and the residue shaken with methylene chloride and 5% aqueous sodium hydroxide. After drying the organic layer and removal of the solvent, the residue is crystallized from diethyl ether-hexane, to yield the α-[5-chloro-2-(1-methyl-4-dimethylaminomethyl-5-pyrazolyl)-phenyl]-2-fluorobenzyl alcohol melting at 125° to 127°; the hydrochloride thereof melts at 225°-230°.

Workup

  1. customIt is evaporated under reduced pressure
  2. customAfter drying
  3. customthe organic layer and removal of the solvent
  4. customthe residue is crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-8b5f13aedfcd4231a02d422b0a99bce6
Source dataset
uspto-grants-1978_07
Patent number
US04099012

Reaction notes

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