Methanol → HCID 69484263, compound

HRID 1075402Notes

Reaction equation

HRID 1075402 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

5

Reactant 3

HCID 887MethanolHCID 7415N,N-DimethylcyclohexylamineHCID 80061-Bromo-3-chloropropane

Product 1

HCID 69484263HCID 69484263, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

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 molest 85%)

Workup

  1. customA one-liter, 3-necked, Morton flask equipped with an air condenser
  2. customReaction
  3. customMethanol was removed by rotary evaporation under reduced pressure
  4. customto yield a brown sludge
  5. customto form
  6. customThe liquid phase was decanted from the oil
  7. additiona second portion of methyl-tert-butylether (600 ml) was added
  8. customliquid phase was decanted off from a thick sludge
  9. additionTo the sludge was added diethylether (600 mL)
  10. customto form
  11. stirringThe mixture was stirred
  12. customa liquid phase was removed

Sources & evidence

ORD record
ord-ae593cf91101446d97c3d07e64a6d5bb
Source dataset
uspto-grants-1999_05
Patent number
US05900475

Reaction notes

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