1-Propanamine, 3-(dibenz[b,e]oxepin-11(6H)-ylidene)-N,N-dimethyl-, hydrochloride (1:1) → Doxepin

HRID 1285337

Reaction equation

HRID 1285337 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]=[C:7]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH3:3].Cl.C(=O)(O)[O-].[Na+]>O>[CH3:1][N:2]([CH2:4][CH2:5][CH:6]=[C:7]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH3:3]

Participants

4

Reactant 2

HCID 146751-Propanamine, 3-(dibenz[b,e]oxepin-11(6H)-ylidene)-N,N-dimethyl-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 3158Doxepin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Doxepin hydrochloride (10 g., 0.032 mol) was dissolved in 50 ml. H2O. Sodium bicarbonate (3.2 g., 0.038 mol) suspended in 25 ml. of H2O was added with stirring, and the mixture stirred for 20 minutes and then extracted 3×50 ml. ether. The ether extracts were combined, dried (Na2SO4) and evaporated in vacuo to yield doxepin as an oil (8.33 g.).

Workup

  1. stirringthe mixture stirred for 20 minutes
  2. extractionextracted 3×50 ml
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c91b9163108f4b619c0fca596a0e1400
Source dataset
uspto-grants-1986_01
Patent number
US04567179

Linked notes

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