Ammonium Chloride → HCID 23142138, compound

HRID 32273Notes

Reaction equation

HRID 32273 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24](=[O:26])[CH3:25])[CH2:18][CH2:17]2)[CH2:3]1.[BH4-].[Na+].[Cl-:30].[NH4+]>CO>[ClH:30].[CH3:27][C:2]1([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5][CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]([OH:26])[CH3:25])[CH2:18][CH2:17]2)[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 231415484-[4-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazin-1-yl]butan-2-one

Product 1

HCID 23142138HCID 23142138, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-[4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-yl]butan-2-one (138 mg, 0.372 mmol) produced in (Example 110) and methanol (1.5 mL) was gradually added sodium borohydride (14.1 mg, 0.372 mmol) at an external temperature of room temperature, followed by stirring for 2 hours under the same conditions. Aqueous solution of ammonium chloride was added to the reaction mixture, and stirring was continued for 20 minutes. After making the mixture basic with aqueous solution of potassium carbonate, extraction was performed with ethyl acetate. The separated organic layer was concentrated under reduced pressure to give a residue, which was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 136 mg of the free form of the title compound as a colorless oil. The free from of the title compound (19 mg, 0.051 mmol) was dissolved in a mixed solvent of ethyl alcohol and ethyl acetate, and then a 4N solution of hydrogen chloride in ethyl acetate (0.014 mL, 0.056 mmol) was added. The mixed solution was concentrated under reduced pressure and the resulting solid residue was washed with a diethyl ether-heptane mixed solvent and then dried under reduced pressure to give 21 mg of the title compound as a colorless solid.

Workup

  1. customat an external temperature of room temperature
  2. stirringstirring
  3. waitwas continued for 20 minutes
  4. extractionbasic with aqueous solution of potassium carbonate, extraction
  5. concentrationThe separated organic layer was concentrated under reduced pressure
  6. customto give a residue, which
  7. customwas purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-d1c315154dab423891fa3756e73d7ef7
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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