Reaction #44793

Reaction equation

bicarbonate

hexahydro-1-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine

methyl 4-bromobutanoate

triethylamine

→

methyl hexahydro-4-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine-1-butanoate

Yield 79.7%

Solvents

THF

Conditions

Workup

1. 1
   Temperaturethe reaction was heated
2. 2
   Temperatureat reflux for 4 hours
3. 3
   Temperatureto cool
4. 4
   WashThe combined ethyl acetate extracts were washed with water
5. 5
   Otherdried
6. 6
   Concentrationconcentrated

Procedure

In a manner similar as described above in Paragraph A, a solution of hexahydro-1-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine (150 mg, 0.506 mmol) and methyl 4-bromobutanoate (0.29 mL, 2.0 mmol) in THF (6 mL) was treated with triethylamine (0.28 mL, 2 mmol) and the reaction was heated at reflux for 4 hours. The reaction was allowed to cool and treated with an aqueous bicarbonate solution. The combined ethyl acetate extracts were washed with water, dried and concentrated to give 0.16 g of methyl hexahydro-4-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine-1-butanoate.

Source