Acetic Acid → 1-[3-(4-Bromo-2-methylphenyl)propyl]-4-methylpiperidine

HRID 734835Notes

Reaction equation

HRID 734835 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[CH3:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH:35]=O)=[C:29]([CH3:37])[CH:28]=1>C1COCC1.CCOC(C)=O>[Br:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][N:23]2[CH2:24][CH2:25][CH:20]([CH3:19])[CH2:21][CH2:22]2)=[C:29]([CH3:37])[CH:28]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 693814-MethylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 822879023-(4-Bromo-2-methylphenyl)propanal

Product 1

HCID 690557421-[3-(4-Bromo-2-methylphenyl)propyl]-4-methylpiperidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.70 g (3.30 mmol) of sodium triacetoxyborohydride and 0.16 mL of glacial acetic acid were added to a solution of 0.32 mL (2.70 mmol) of 4-methylpiperidine and 0.60 g (2.64 mmol) of 3-(4-bromo-2-methylphenyl)propionaldehyde in 10 mL of THF and the mixture was stirred for 2 hours at RT. The reaction mixture was diluted with EtOAc, and the organic phase was washed with semisaturated aqueous sodium bicarbonate solution washed, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 0.65 (78% of theoretical); C16H24BrO (M=310.273); calc.: molpeak (M+H)+: 310/312 (Br); found: molpeak (M+H)+: 310/312 (Br); Rf value: 0.28 (silica gel, PE/EtOAc 3:2).

Workup

  1. washthe organic phase was washed with semisaturated aqueous sodium bicarbonate solution
  2. washwashed
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down in vacuo

Sources & evidence

ORD record
ord-a793727ac3a44ad4bed9ba25014643fe
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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