Hydrochloric Acid → HCID 9890146, compound

HRID 1582745Notes

Reaction equation

HRID 1582745 reaction equation
[BH4-].[Li+].[C:3]([C:5]([C:28]1[CH:33]=[CH:32][C:31]([C:34](OC)=[O:35])=[CH:30][CH:29]=1)([CH:25]([CH3:27])[CH3:26])[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:11][CH2:10]1)#[N:4].Cl>O1CCCC1>[C:3]([C:5]([C:28]1[CH:29]=[CH:30][C:31]([CH2:34][OH:35])=[CH:32][CH:33]=1)([CH:25]([CH3:27])[CH3:26])[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:11][CH2:10]1)#[N:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 22718310HCID 22718310, compound

Product 1

HCID 9890146HCID 9890146, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (3 mg) was added to a tetrahydrofuran solution (2 ml) containing the 1-[4-cyano-5-methyl-4-(4-carbomethoxyphenyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazine (64 mg) obtained in Example 12, and the mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, then 1 N hydrochloric acid (1 ml) was added thereto, and the mixture was stirred at room temperature for 10 minutes. The organic layer was partitioned by adding aqueous saturated sodium bicarbonate and ethyl acetate, washed with water, and dried over sodium sulfate anhydrous. The residue obtained by evaporation was purified by Cromatorex NH silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (57 mg, 95%) as a colorless oil. 4 N hydrogen chloride/ethyl acetate solution was added at room temperature to a solution of this free compound (27 mg) in methanol. The solution was stirred for 10 minutes, and then the solvent was evaporated, whereby the hydrochloride (31 mg) of the title compound was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe organic layer was partitioned
  4. additionby adding aqueous saturated sodium bicarbonate and ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate anhydrous
  7. customThe residue obtained by evaporation
  8. customwas purified by Cromatorex NH silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-badde66f3af9436f9648080984745b44
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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