Water → 2-Bromo-1-(3,3-dimethylpiperidin-1-yl)ethanone

HRID 1081263Notes

Reaction equation

HRID 1081263 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[Br:16][CH2:17][C:18](Br)=[O:19].O>ClCCl>[Br:16][CH2:17][C:18]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:8])([CH3:1])[CH2:3]1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 709423,3-Dimethylpiperidine

Product 1

HCID 233637862-Bromo-1-(3,3-dimethylpiperidin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3,3-dimethylpiperidine (10 g) and triethylamine (12.3 ml) in dry dichloromethane (50 ml) was added dropwise to an ice-cold solution of bromoacetyl bromide (7.7 ml) in dry dichloromethane (100 ml). The mixture was stirred at 23° for 18 h then recooled to 0°. Iced water (200 ml) was added and the layers separated. The aqueous layer was further extracted with dichloromethane (2×200 ml) then the combined extracts were washed with 2N HCl (200 ml) and saturated brine (200 ml), dried and evaporated to give the title compound (17.28 g) as a brown oil.

Workup

  1. customthen recooled to 0°
  2. customthe layers separated
  3. extractionThe aqueous layer was further extracted with dichloromethane (2×200 ml)
  4. washthe combined extracts were washed with 2N HCl (200 ml) and saturated brine (200 ml)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-5beeb1997e18405f880f927d73122255
Source dataset
uspto-grants-1996_12
Patent number
US05585376

Reaction notes

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