Hydrochloric Acid → Phenacylamine

HRID 2367349Notes

Reaction equation

HRID 2367349 reaction equation
[Br-].[O:2]=[C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:4][N+:5]12CN3CN(CN(C3)C1)C2.[ClH:21]>C(O)C>[ClH:21].[NH2:5][CH2:4][C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 137167301-(2-Oxo-2-phenylethyl)-1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decan-1-ium bromide

Product 2

HCID 313Hydrochloric AcidHCID 11952PhenacylamineYield 129.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(2-oxo-2-phenylethyl)-3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decane bromide (3.3 g, 9.73 mmol) was suspended in a mixture of ethanol (50 mL) and hydrochloric acid (4.93 mL, 58.4 mmol) and heated at reflux in ethanol (50 mL) for 1.5 hours. The mixture was cooled to 0° C., filtered, and washed by ethanol (30 mL). The organic phase was evaporated to afford an HCl salt of the title compound (1.7 g) as a pale yellow solid. LC-MS (ES) m/z=136 [M+H]+.

Workup

  1. temperatureheated
  2. filtrationfiltered
  3. washwashed by ethanol (30 mL)
  4. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-af4d49d7b28445c8974652ef90dc7a04
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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