Hydrochloric Acid → (1S)-1-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one--hydrogen chloride (1/1)

HRID 2376625Notes

Reaction equation

HRID 2376625 reaction equation
C(O)(=O)[C@@H](C1C=CC=CC=1)O.[NH2:12][C@H:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][CH2:16][N:15]([CH3:24])[C:14]1=[O:25].[ClH:26]>C(OCC)(=O)C>[ClH:26].[NH2:12][C@H:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][CH2:16][N:15]([CH3:24])[C:14]1=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131727233HCID 131727233, compound

Product 1

HCID 44178389(1S)-1-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one--hydrogen chloride (1/1)Yield 92.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

(S)-1-Amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one (R)-mandelic acid salt (2.42 g, 7.06 mmol, 98.4% ee) was slurried in 25 mL ethyl acetate at ambient temperature. Concentrated aqueous hydrochloric acid (1.1 mL, about 11.2 mmol) was added and the mixture was heated to 50° C. with vigorous stirring for 3.5 hours. The slurry was cooled to ambient temperature and filtered, rinsed with the methyl t-butyl ether (about 10 mL) to give 1.48 g of the title compound (92.5% yield, 97.9% ee).

Workup

  1. temperatureThe slurry was cooled to ambient temperature
  2. filtrationfiltered
  3. washrinsed with the methyl t-butyl ether (about 10 mL)

Sources & evidence

ORD record
ord-cee1598c20e747b885863a5f4e025e71
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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