HCID 20274169, compound → Dipropyldopamine hydrobromide

HRID 371066Notes

Reaction equation

HRID 371066 reaction equation
B(Br)(Br)[Br:2].C(Cl)Cl.[CH2:8]([N:11]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[C:19]([O:25]C)[CH:18]=1)[CH2:12][CH2:13][CH3:14])[CH2:9][CH3:10]>C(Cl)Cl>[BrH:2].[OH:25][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[OH:23])[CH2:16][CH2:15][N:11]([CH2:8][CH2:9][CH3:10])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 20274169HCID 20274169, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 11957536Dipropyldopamine hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution (150 ml.) of boron tribromide/methylene chloride (1 g./5 ml., 0.12 mole) was added to a solution of 5.0 g. (0.019 mole) of N,N-di-(n-propyl)-3,4-dimethoxyphenethylamine in 100 ml. of methylene chloride, cooled in an ice bath. The bath was removed and the reaction mixture was stirred at room temperature. Methanol (about 50 ml.) was added to the reaction mixture, with cooling, and the resulting solution was evaporated in vacuo. The residue crystallized to give 3,4-dihydroxy-N,N-di-(n-propyl)phenethylamine hydrobromide, m.p. 153.5°-154.5° C.

Workup

  1. customThe bath was removed
  2. additionMethanol (about 50 ml.) was added to the reaction mixture
  3. temperaturewith cooling
  4. customthe resulting solution was evaporated in vacuo
  5. customThe residue crystallized

Sources & evidence

ORD record
ord-0f406bde98394b7caceb55654d04f5fd
Source dataset
uspto-grants-1985_07
Patent number
US04529604

Reaction notes

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