4-((S)-4-Chloro-1-methoxy-2-nitro-6,7-dihydro-5H-benzocyclohepten-7-yl)-morpholine → (S)-1-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine

HRID 1687476Notes

Reaction equation

HRID 1687476 reaction equation
Cl[C:2]1[C:12]2[CH2:11][CH2:10][C@H:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:8]=[CH:7][C:6]=2[C:5]([O:19][CH3:20])=[C:4]([N+:21]([O-])=O)[CH:3]=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH3:20][O:19][C:5]1[C:6]2[CH2:7][CH2:8][C@@H:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH2:10][CH2:11][C:12]=2[CH:2]=[CH:3][C:4]=1[NH2:21]

Participants

5

Reactant 2

HCID 672640024-((S)-4-Chloro-1-methoxy-2-nitro-6,7-dihydro-5H-benzocyclohepten-7-yl)-morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 56954474(S)-1-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-((S)-4-Chloro-1-methoxy-2-nitro-6,7-dihydro-5H-benzocyclohepten-7-yl)-morpholine (12 mg, 0.035 mmol) and 20% Pd(OH)2/C (9 mg) in Methanol (4 mL), was placed under a blanket of Hydrogen at atmospheric pressure. After 16 h, the reaction was filtered and concentrated under reduced pressure to give (S)-1-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine.

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-24e4570a487e4382b16e8819ef63f4a1
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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