Hydrochloric Acid → 5-(3-[(2-chloro-1-oxo-ethyl)methylamino]propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine

HRID 1647007Notes

Reaction equation

HRID 1647007 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2.C(N(CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31].Cl>ClCCl>[Cl:28][CH2:29][C:30]([N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2995DesipramineHCID 6577Chloroacetyl chlorideHCID 8471Triethylamine

Product 1

HCID 541516295-(3-[(2-chloro-1-oxo-ethyl)methylamino]propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 5-(3-methylaminopropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (7.0 g, 0.026 mol) and triethylamine (4 mL) in dichloromethane (100 mL) and cool with an ice-bath. Add, by dropwise addition, a solution of chloroacetyl chloride (3.23 g, 0.0286 mol) in dichloromethane (25 mL). Stir at room temperature for 12 hours, shake with dilute hydrochloric acid and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound as an oil.

Workup

  1. temperaturecool with an ice-bath
  2. additionAdd, by dropwise addition
  3. dry with materialdry (MgSO4)
  4. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-872fb14a53a543a7bdc4ab7d5d6600e5
Source dataset
uspto-grants-1993_01
Patent number
US05182387

Reaction notes

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