Chloride → 1-(11-bromoundecanoyl)-N,N,beta,beta-tetramethyl-4-piperidineethanamine

HRID 977166Notes

Reaction equation

HRID 977166 reaction equation
[Cl-].[Br:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O.[CH3:16][N:17]([CH3:28])[CH2:18][C:19]([CH3:27])([CH3:26])[CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>ClC(Cl)Cl.O>[Br:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:23]1[CH2:24][CH2:25][CH:20]([C:19]([CH3:27])([CH3:26])[CH2:18][N:17]([CH3:16])[CH3:28])[CH2:21][CH2:22]1)=[O:15]

Participants

7

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 1781211-Bromoundecanoic acidHCID 10921200Dimethyl[2-methyl-2-(piperidin-4-yl)propyl]amine

Product 1

HCID 152943761-(11-bromoundecanoyl)-N,N,beta,beta-tetramethyl-4-piperidineethanamineYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

17.5 g (6.2×10-2 mole) of the chloride of 11-bromoundecanoic acid diluted in 100 ml of trichloromethane was added dropwise to a solution of N,N,β,β-tetramethyl-4-piperidineethanamine in 120 ml of trichloromethane and 19.2 ml (14.7×10-2 mole) of N,N-diethylethanamine, cooled to 0° C. The reaction mixture was stirred for 3 hours at 0° C. then for 20 hours at room temperature. The reaction mixture was poured into water and allowed to settle. The organic phase was recovered and dried over magnesium sulphate and the solvents were evaporated off under reduced pressure. 12 g (yield: 57%) of the desired product was obtained as an oil.

Workup

  1. waitfor 20 hours at room temperature
  2. customThe organic phase was recovered
  3. dry with materialdried over magnesium sulphate
  4. customthe solvents were evaporated off under reduced pressure

Sources & evidence

ORD record
ord-087ed9419eea4bf3bd61bb115351c542
Source dataset
uspto-grants-1997_03
Patent number
US05614534

Reaction notes

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