Hexamethylenetetramine → 1-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide

HRID 1627338Notes

Reaction equation

HRID 1627338 reaction equation
[Br:1][CH2:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5].C1N2CN3CN(C2)C[N:17]1C3>C(Cl)Cl>[BrH:1].[NH2:17][CH2:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 4101HexamethylenetetramineHCID 212583981-Bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one

Product 1

HCID 667410091-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromideYield 158.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one (4.0 g, 13 mmol) and HMTA (hexamethylenetetramine, 2.0 g, 14 mmol) in DCM (25 mL) was stirred 48 h at room temperature. The volatiles were evaporated in vacuo. The crude material was dissolved in EtOH (80 mL) and combined with conc HCl (40 mL). The resulting mixture was heated at reflux 2 h, cooled to room temperature, and concentrated in vacuo to give 1-amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide (6.75 g), which was used in the next reaction without purification. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (bs, 3H), 7.61 (d, 1H), 7.52 (d, 1H), 7.29 (dd, 1H), 3.94 (m, 2H), 1.47 (s, 6H).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionThe crude material was dissolved in EtOH (80 mL)
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux 2 h
  5. temperaturecooled to room temperature
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-500becc97c194af99e23470c9e1eb63d
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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