Hydrochloric Acid → (7S,10aR,Z)-7-amino-1,2,3,4,7,8-hexahydropyrido[1,2-a]azepin-6(10aH)-one hydrochloride

HRID 529527Notes

Reaction equation

HRID 529527 reaction equation
[ClH:1].[O:2]=[C:3]1[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:8]2[CH:7]=[CH:6][CH2:5][C@@H:4]1[NH:14]C(=O)OC(C)(C)C>O1CCOCC1>[ClH:1].[NH2:14][C@@H:4]1[C:3](=[O:2])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:8]2[CH:7]=[CH:6][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86706214tert-butyl (7S,10aR,Z)-6-oxo-1,2,3,4,6,7,8,10a-octahydropyrido[1,2-a]azepin-7-ylcarbamate

Product 1

HCID 68292606(7S,10aR,Z)-7-amino-1,2,3,4,7,8-hexahydropyrido[1,2-a]azepin-6(10aH)-one hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl (4.0 N in 1,4-dioxane, 2.33 mL, 9.32 mmol) was added to a 0° C. solution of tert-butyl (7S,10aR,Z)-6-oxo-1,2,3,4,6,7,8,10a-octahydropyrido[1,2-a]azepin-7-ylcarbamate (653 mg, 2.33 mmol) in 1,4-dioxane (0.93 mL). The reaction mixture was then stirred at rt for 1 hr. The reaction mixture was concentrated and dried under vacuum to give (7S,10aR,Z)-7-amino-1,2,3,4,7,8-hexahydropyrido[1,2-a]azepin-6(10aH)-one hydrochloride (504 mg, 2.33 mmol, 100% yield) as a tan solid. Anal. Calcd. for C10H16N2O m/z 180.2. found: 181.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-b072d230c9fa4974802d10ca5a2d0737
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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