Acetic Acid → 1-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine

HRID 447306Notes

Reaction equation

HRID 447306 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:15][NH:16][CH3:17].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO.C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:16]([CH3:17])[CH3:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 246921481-(4-Bromophenyl)piperidin-4-one

Product 1

HCID 667303771-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a mixture of 1-(4-bromophenyl)piperidin-4-one (200 mg, 0.79 mmol), dimethylamine (0.80 mL, 1.57 mmol, 2M in THF), and acetic acid (0.20 mL, 3.15 mmol) in DCE (8 mL) was added sodium triacetoxyborohydride (250 mg, 1.18 mmol) at rt. The resulting mixture was stirred at rt for 2.5 h. The reaction was quenched with sat. NaHCO3 solution, extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated to give a yellow oil. The title compound was isolated by silica gel chromatography (EtOAc to MeOH/CH2Cl2, 35:100) as a yellow solid (139 mg, 63%). 1H NMR (400 MHz, CD3OD) δ 7.31 (d, J=9.0 Hz, 2H), 6.88 (d, J=9.0 Hz, 2H), 3.76-3.73 (m, 2H), 2.69 (t, J=12.3 Hz, 2H), 2.53-2.45 (m, 1H), 2.41 (s, 6H), 2.01-1.98 (m, 2H), 1.67-1.57 (m, 2H); MS ESI 283.0 [M+H]+, calcd for [C13H19BrN2+H]+ 283.07.

Workup

  1. customThe reaction was quenched with sat. NaHCO3 solution
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-6e01a4dd59ee4a34b29330c1e4d8657e
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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