6-Dimethylaminohexan-1-ol → Ammonium Hydroxide

HRID 621765

Reaction equation

HRID 621765 reaction equation
[CH2:1]([N:13]=[C:14]=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:16][N:17]([CH3:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]>O1CCCC1>[NH4+:13].[OH-:15].[CH3:16][N:17]([CH3:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:14](=[O:15])[NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 746236-Dimethylaminohexan-1-olHCID 77873Dodecane, 1-isocyanato-

Product 2

HCID 14923Ammonium HydroxideHCID 14407596Dodecylcarbamic acid 6-(dimethylamino)hexyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 gm (5 meq) of dodecyl isocyanate and 726 mg (5 meq) of 6-(dimethylamino)hexanol are combined in 5 ml of tetrahydrofuran and reacted over weekend at room temperature. The insoluble crystals are filtered, washed with ethyl acetate and the filtrate and washings combined, evaporated under reduced pressure (<30° C.) and dried in vacuo. The product is purified by silica gel chromatography in the system CH2Cl2 :CH3OH:NH4OH (65:25:4). Fractions 34-46 are combined, evaporated and dried in vacuo to yield 300 mg (Rf 0.9 S.G. CH2Cl2, CH3OH, NH4OH) of title compound.

Workup

  1. customreacted over weekend at room temperature
  2. filtrationThe insoluble crystals are filtered
  3. washwashed with ethyl acetate
  4. customevaporated under reduced pressure (<30° C.)
  5. customdried in vacuo
  6. customThe product is purified by silica gel chromatography in the system CH2Cl2 :CH3OH:NH4OH (65:25:4)
  7. customevaporated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-10fe8ebfd8054af49d4995ba11d7035c
Source dataset
uspto-grants-1989_04
Patent number
US04824996

Linked notes

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