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

HRID 83853Notes

Reaction equation

HRID 83853 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-608e79795a264ebd832ad3810ac0fb79
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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