Hydrochloric Acid → (S)-4-amino-1,2,4,5-tetrahydro-3H-benzo[c]azepin-3-one hydrochloride

HRID 11600Notes

Reaction equation

HRID 11600 reaction equation
C(OC([NH:8][C@H:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[CH2:12][NH:11][C:10]1=[O:20])=O)(C)(C)C.[ClH:21]>C(OCC)C>[ClH:21].[NH2:8][C@H:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[CH2:12][NH:11][C:10]1=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69195282tert-Butyl (S)-(3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl)carbamate

Product 1

HCID 69196954(S)-4-amino-1,2,4,5-tetrahydro-3H-benzo[c]azepin-3-one hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(S)-4-(t-butyloxycarbonylamino)-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one (276 mg) was dissolved in 2 M hydrogen chloride in diethyl ether solution (25 mL) at room temperature. A precipitate slowly formed. After 16 h stirring the solvent was evaporated under vacuum. The residue was twice taken up in toluene (10 mL) and evaporated to provide (S)-4-amino-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one hydrochloride, which was used directly in the next step.

Workup

  1. customA precipitate slowly formed
  2. customwas evaporated under vacuum
  3. customevaporated

Sources & evidence

ORD record
ord-da942735b7e648a3ac69568f23773259
Source dataset
uspto-grants-2006_08
Patent number
US07098235B2

Reaction notes

Loading…