Methanol → HCID 69484263, compound
Reaction equation
[CH3:1][N:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:3].[Br:10][CH2:11][CH2:12][CH2:13][Cl:14].CO>C(OC)(C)(C)C>[Br-:10].[Cl:14][CH2:13][CH2:12][CH2:11][N+:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([CH3:3])[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A one-liter, 3-necked, Morton flask equipped with an air condenser and a magnetic stirring plate was charged with N,N-dimethylcyclohexylamine (210.06 grams, 1.65 moles), 1-bromo-3-chloropropane (259.99 grams, 1.65 moles) and methanol (250 mL). Reaction was maintained at 65° C. for 24 hours. Methanol was removed by rotary evaporation under reduced pressure to yield a brown sludge. To the sludge was added tert-butylmethylether (600 ml) causing an oil to form. The liquid phase was decanted from the oil and a second portion of methyl-tert-butylether (600 ml) was added. The mixture was stirred and liquid phase was decanted off from a thick sludge. To the sludge was added diethylether (600 mL) causing a white, semi-solid layer to form. The mixture was stirred and a liquid phase was removed. A white solid was placed in a vacuum oven at 35° C. for 24 hours. Yield 404.9 grams (1.42 moles, 85%).
Workup
- customA one-liter, 3-necked, Morton flask equipped with an air condenser
- customReaction
- customMethanol was removed by rotary evaporation under reduced pressure
- customto yield a brown sludge
- customto form
- customThe liquid phase was decanted from the oil
- additiona second portion of methyl-tert-butylether (600 ml) was added
- customliquid phase was decanted off from a thick sludge
- additionTo the sludge was added diethylether (600 mL)
- customto form
- stirringThe mixture was stirred
- customa liquid phase was removed
Sources & evidence
- ORD record
- ord-a7411af382d942dfb5a5707881f85dd5
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05969090
Reaction notes
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