Hydrochloric Acid → 1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropylamine

HRID 1250539Notes

Reaction equation

HRID 1250539 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13](=O)[CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH:13]([NH2:28])[CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 222577801-[1-(3,4-Dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone

Product 1

HCID 222576661(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropylamineYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone (0.16 g, 0.49 mmol) in methanol (1.5 ml) was added ammonium acetate (0.38 g, 4.93 mmol), followed by sodium cyanoborohydride (31 mg, 0.5 mmol) and the resulting solution was stirred at room temperature. After 48 h, hydrochloric acid (conc.) was added until pH was 2 and the volatiles were removed under vacuum. The residue was dissolved in water and washed with ethyl acetate. The aqueous layer was then basified to pH>10 and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated to give 1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropylamine(0.16 g) as an oil which was used in the next step without further purification.

Workup

  1. customthe volatiles were removed under vacuum
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-95a750301712404aa146e3a4f2e1b19c
Source dataset
uspto-grants-2002_01
Patent number
US06339087B1

Reaction notes

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