Hydrochloric Acid → 1-(2-Chlorophenyl)-3-(dimethylamino)propan-1-one--hydrogen chloride (1/1)

HRID 1907261Notes

Reaction equation

HRID 1907261 reaction equation
Cl.[NH:2]([CH3:4])[CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH3:13].[CH2:15]=O>C(O)C>[ClH:5].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH2:13][CH2:3][N:2]([CH3:15])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 72864Ethanone, 1-(2-chlorophenyl)-

Product 1

HCID 241872721-(2-Chlorophenyl)-3-(dimethylamino)propan-1-one--hydrogen chloride (1/1)Yield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At 0° C., concentrated HCl was added dropwise to Me2NH (40% in water, 5.57 mL, 1.1 equiv) to acidify the amine. After the addition, 1-(2-chlorophenyl)ethanone (6.18 g, 0.04 mol) and paraformaldehyde (1.68 g, 1.4 equiv) were added. The mixture was dissolved in ethanol (20 mL) and heated to reflux for 30 h. LC-MS found the starting material was gone. The reaction mixture was cooled to rt. The volatiles were removed in vacuo. EtOAc (30 mL) was added and the suspension was stirred for 15 min. The solid was collected by filtration and washed with EtOAc (2×5 mL). The white solid was dried under vacuum to afford 1-(2-chlorophenyl)-3-(dimethylamino)propan-1-one HCl salt (5.17 g, 61% yield). LC-MS (3 min) tR=0.72 min, m/z 212, 214(M+1).

Workup

  1. additionwere added
  2. temperatureheated
  3. temperatureto reflux for 30 h
  4. customThe volatiles were removed in vacuo
  5. additionEtOAc (30 mL) was added
  6. filtrationThe solid was collected by filtration
  7. washwashed with EtOAc (2×5 mL)
  8. customThe white solid was dried under vacuum

Sources & evidence

ORD record
ord-199801534e604fff9807cd213e92d7ce
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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