Sodium borohydride → HCID 15886821, compound

HRID 1602855Notes

Reaction equation

HRID 1602855 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3([N:24]4[CH2:29][CH2:28][N:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:26][CH2:25]4)[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]3)[CH:12]=2)=[O:9])[CH2:4][CH2:3]1.[BH4-].[Na+]>CCO>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3([N:24]4[CH2:25][CH2:26][N:27]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:28][CH2:29]4)[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]3)[CH:12]=2)=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 9869513HCID 9869513, compound

Product 1

HCID 15886821HCID 15886821, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(oxo)-N-[3-[4-methyl-1-(4-phenyl-1-pipera-zinyl)cyclohexyl]phenyl]-1-piperidinecarboxamide (cis isomer) (34 mg, 0.072 mmol) in anhydrous EtOH was treated with excess NaBH4 (14 mg, 0.36 mmol) and the resulting solution was stirred at room temperature for 1 h. The reaction was quenched with excess saturated NH4Cl (aq.) then extracted with EtOAc (3×). The combined extracts were dried (Na2SO4), concentrated under reduced pressure, and triturated with 30% EtOAc/hexanes to give 4-(hydroxy)-N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)-cyclohexyl]phenyl]-1-piperidinecarboxamide (cis isomer), as a white powder. The HCl salt was prepared by adding excess saturated EtOAc/HCl solution to the free base in dry MeOH. Concentration of the homogeneous solution yielded a white solid which was washed with EtOAc. mp=144-145° C.

Workup

  1. customThe reaction was quenched with excess saturated NH4Cl (aq.)
  2. extractionthen extracted with EtOAc (3×)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customtriturated with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-d42884c6f55847b1a0b6b81a1e28b197
Source dataset
uspto-grants-1999_11
Patent number
US05985873

Reaction notes

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