1-Butanol → 1-benzhydrylazetidine

HRID 1089562Notes

Reaction equation

HRID 1089562 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](O)[CH2:8][CH2:9]C.BrCCCCl.[CH:17]([NH2:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.C1(C)C=CC=CC=1>[CH:17]([N:30]1[CH2:9][CH2:8][CH2:7]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 7036BenzhydrylamineHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 28028951-benzhydrylazetidineYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To A solution of 6.9 kg (50 moles) of potassium carbonate in 7.5 liters of water was added 18.5 liters of 1-butanol, 7.85 kg (50 moles) of 1-bromo-3-chloropropane and 5.18 kg (25 moles) of benzhydrylamine (97% purity with 10% toluene as a residual solvent). The reaction mixture was heated to 100° C. externally with steam and stirred slowly under a nitrogen gas atmosphere overnight. About 12 liters of water was added to the mixture to dissolve some inorganic salt precipitate. The layers were separated and organic layer was distilled under reduced pressure to remove about 18 liters of butanol and water. To the residue was added 1.5 liters of methanol and the resulting mixture was stirred slowly while cooling down to room temperature. The white solid was collected by filtration, rinsed twice with 700 ml portions of methanol and dried in a vacuum oven to give 4.2 kg (75%) of product, m.p. 107°-109° C. The NMR analysis obtained was as follows:

Workup

  1. dissolutionto dissolve some inorganic salt precipitate
  2. customThe layers were separated
  3. distillationorganic layer was distilled under reduced pressure
  4. customto remove about 18 liters of butanol and water
  5. additionTo the residue was added 1.5 liters of methanol
  6. stirringthe resulting mixture was stirred slowly
  7. temperaturewhile cooling down to room temperature
  8. filtrationThe white solid was collected by filtration
  9. washrinsed twice with 700 ml portions of methanol
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8e4c97ab35664c69937ba9213d263e2a
Source dataset
uspto-grants-1990_10
Patent number
US04966979

Reaction notes

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