Methylamine → 11-(Methylamino)undecan-1-ol

HRID 1052938Notes

Reaction equation

HRID 1052938 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[CH3:14][NH2:15]>C(O)C>[CH3:14][NH:15][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 7416311-Bromo-1-undecanol

Product 1

HCID 1976727411-(Methylamino)undecan-1-olYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11-bromoundecanol (25.12 g, 0.10 mol) and methylamine (41% in water, 127 ml, 1.50 mol) in ethanol (50 ml) was heated for 7 h to 70° C. and stirred for a further 16 h at ambient temperature. The solvent was distilled off. After cooling the white solid was dissolved in caustic soda (2N, 200 ml) and diethyl ether (300 ml). The phases were separated and the aqueous phase was extracted with diethyl ether (2×100 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was recrystallized from diethyl ether. 13.23 g (65.7 mmol, 67% yield) of a while solid (melting point: 58° C.) was obtained.

Workup

  1. distillationThe solvent was distilled off
  2. temperatureAfter cooling the white solid
  3. dissolutionwas dissolved in caustic soda (2N, 200 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with diethyl ether (2×100 ml)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated on the rotary evaporator
  9. customThe crude product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-37f1f55fa8c34964ae58c3100ebe2b4d
Source dataset
uspto-grants-2016_07
Patent number
US09393181B2

Reaction notes

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