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

HRID 1670418Notes

Reaction equation

HRID 1670418 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][C@H:4]([NH:13]C(=O)OC(C)(C)C)[C:3]1=[O:21].[ClH:22]>O1CCOCC1>[ClH:22].[NH2:13][C@H:4]1[CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3]1=[O:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57443396tert-butyl [(3S)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]carbamate

Product 1

HCID 67345769(S)-3-Amino-1-methyl-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.36 g of 7a (15.01 mmol) are taken up in a 250 ml round-bottomed flask and 110 ml of a solution of hydrochloric acid in dioxane (4M) are added. The mixture is stirred for 4 h at AT under argon. After the solvent has been evaporated off, the solid is disintegrated with 25 ml of isopropyl ether, and filter-dried over sintered glass. After drying, 3.1 g of amine 8a in hydrochloride form are obtained, which amine is used directly for the following step.

Workup

  1. customAfter the solvent has been evaporated off
  2. customfilter-dried over sintered glass
  3. customAfter drying

Sources & evidence

ORD record
ord-659427a0d0204af2998cfc534f12ed08
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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