tert-Butyl methyl ether → Methyl 7-amino-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 488379Notes

Reaction equation

HRID 488379 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-])=O.C(OC)(C)(C)C>[Pd].C(O)C>[NH2:1][C:4]1[CH:18]=[CH:17][C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 22219595HCID 22219595, compound

Product 1

HCID 22269653Methyl 7-amino-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the compound from Step 1 (50 g, 200 mmol) and 10% palladium on carbon (2.5 g) in ethanol (800 mL) is hydrogenated with shaking at 20 psi. Methyl t-butyl ether is added and the mixture filtered through celite and concentrated to give 44 g (100%) of the title compound as a white solid, mp 100-104° C.

Workup

  1. filtrationthe mixture filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bb34db5a90214c42b9dc7a62138a3b73
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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