2-Aminomethyl-1-ethylpyrrolidine → 2-((3,5-Dibromo-2,6-dimethoxybenzamido)methyl)-1-ethylpyrrolidine hydrochloride

HRID 224423

Reaction equation

HRID 224423 reaction equation
Cl.[CH2:2]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH:10]C(=O)C1C(OC)=CC=C([Cl:20])C=1OC)[CH3:3].[Br:24][C:25]1[C:26]([O:37][CH3:38])=[C:27]([C:31]([O:35][CH3:36])=[C:32]([Br:34])[CH:33]=1)[C:28]([OH:30])=O.NCC1CCCN1CC>S(Cl)(Cl)=O>[ClH:20].[CH2:2]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH:10][C:28](=[O:30])[C:27]1[C:31]([O:35][CH3:36])=[C:32]([Br:34])[CH:33]=[C:25]([Br:24])[C:26]=1[O:37][CH3:38])[CH3:3]

Participants

5

Reactant 3

HCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 15565714N-Ethyl-2-(3-chloro-2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochlorideHCID 155657343,5-Dibromo-2,6-dimethoxybenzoic acid

Product 1

HCID 155657122-((3,5-Dibromo-2,6-dimethoxybenzamido)methyl)-1-ethylpyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Using the same method as for compound of Example 8 this compound is prepared from 20.4 g (0.06 mol) of 3,5-dibromo-2,6-dimethoxybenzoic acid, 50 ml of thionyl chloride and 7.7 g (0.06 mol) of 2-(aminomethyl)-1-ethylpyrrolidine. The obtained product is recrystallized from ethanol-ethyl ether. Yield: 20.2 g, m.p. 164°-65° C. The free base is precipitated from the water solution of the hydrochloric salt by the addition of sodium hydroxide, m.p. 133°-134° C.

Workup

  1. customThe obtained product is recrystallized from ethanol-ethyl ether
  2. customThe free base is precipitated from the water solution of the hydrochloric salt by the addition of sodium hydroxide, m.p. 133°-134° C.

Sources & evidence

ORD record
ord-78d54878815845c2814a9c35537df05d
Source dataset
uspto-grants-1980_11
Patent number
US04232037

Linked notes

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