Hydrogen Bromide → 1-Benzyl-1,4-diazepane

HRID 704389

Reaction equation

HRID 704389 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11](C(OCC)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br>O>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 54118699Ethyl 4-benzylhomopiperazine-1-carboxylate

Product 1

HCID 2283651-Benzyl-1,4-diazepaneYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.85 g of ethyl 4-benzylhomopiperazine-1-carboxylate and 5 ml of 47% hydrobromic acid was heated at 100° C. for 10 hours. After addition of a small amount of water, the reaction mixture was washed with ethyl acetate. The aqueous layer was made alkaline with 30% sodium hydroxide and, after salting out with sodium chloride, extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.55 g of 1-benzylhomopiperazine.

Workup

  1. washthe reaction mixture was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d4cbe5d0ee0429bb7fd06053c051ddc
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Linked notes

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