Methylamine → 6-(N-methyl-N-Carbobenzyloxyamino)-hexan-1-ol

HRID 433887Notes

Reaction equation

HRID 433887 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[CH3:9][NH2:10].[C:11](Cl)([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C1COCC1.CCOCC>[CH3:9][N:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 10387Benzyl chloroformateHCID 779706-Bromo-1-hexanol

Product 1

HCID 187560556-(N-methyl-N-Carbobenzyloxyamino)-hexan-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Unsymmetrical Primary/Secondary diamine: 6-(N-methyl-N-Carbobenzyloxyamino)-hexan-1-ol was synthesized as follows. To a solution of 6-bromo-hexan-1-ol (2.0 g, 17.4 mmol) was added 50 mL of a 2.0 M solution of methylamine (˜10 eq.) in THF and the reaction was allowed to stir overnight. The reaction mixture was diluted with 30 mL of ether, filtered, and concentrated. The crude material was then diluted in 30 mL of ether and 50 mL of saturated NaHCO3 solution. Carbobenzyloxychloride (2.5 g, 51 mmol) was then added and the reaction mixture was stirred vigorously for 2 hours. The reaction was then diluted with 100 mL of ether, washed with brine, dried over MgSO4, filtered and concentrated. Silica gel chromatography (10-50% EtOAc:hexanes) afforded 3.1 g (76%) of product as a clear oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe crude material was then diluted in 30 mL of ether
  4. stirringthe reaction mixture was stirred vigorously for 2 hours
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e3957711c6f54b82b20ac2d5a570f8ba
Source dataset
uspto-grants-2003_12
Patent number
US06670348B1

Reaction notes

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