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

HRID 529528Notes

Reaction equation

HRID 529528 reaction equation
[ClH:1].[NH2:2][C@@H:3]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:7]2[CH:6]=[CH:5][CH2:4]1.[H][H]>CO.[Pd]>[ClH:1].[NH2:2][C@@H:3]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:7]2[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 68292606(7S,10aR,Z)-7-amino-1,2,3,4,7,8-hexahydropyrido[1,2-a]azepin-6(10aH)-one hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 86706215(7S,10aR)-7-aminooctahydropyrido[1,2-a]azepin-6(7H)-one hydrochlorideYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To round bottom flask, 10% Pd/C (35 mg, 0.022 mmol) was added to a solution of (7S,10aR,Z)-7-amino-1,2,3,4,7,8-hexahydropyrido[1,2-a]azepin-6(10aH)-one hydrochloride (3.23 gm, 1.49 mmol) in MeOH (5 mL). A hydrogen atmosphere was introduced via balloon and the reaction mixture was stirred for 3 hr. The reaction mixture was diluted with MeOH and filtered. The filtrate was concentrated and the residue was dried under vacuum to give (7S,10aR)-7-aminooctahydropyrido[1,2-a]azepin-6(7H)-one hydrochloride (299 mg, 1.37 mmol, 92% yield) as a light yellow solid. Anal. Calcd. for C10H18N2O m/z 182.2. found: 183.0 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-aacea4152e194c2394332d5014e0fee2
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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