HCID 67264195, compound → HCID 67265074, compound

HRID 1688037Notes

Reaction equation

HRID 1688037 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH:5]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:4]1)[CH3:2]>[Pd].C(O)C>[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH:5]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 67264195HCID 67264195, compound

Product 1

HCID 67265074HCID 67265074, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9-Ethyl-7-morpholin-4-yl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (59 mg, 0.19 mmol) and 10% Palladium on Carbon (50% Wet) (25 mg) in Ethanol (10 mL) was shaken under an atmosphere of Hydrogen (40 psi) for 6 h. 9-Ethyl-7-morpholin-4-yl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-2-ylamine (46 mg, 86%) was isolated following filtration and concentration. 1H-NMR (CDCl3): 6.64 (d, 1H, J=8.4 Hz), 6.06 (s, 1H), 6.00 (d, 1H, J=8.4 Hz), 4.28 (m, 1H), 4.12 (m, 1H), 3.69 (m, 5H), 3.23 (m, 3H), 2.95 (m, 1H), 2.66 (m, 4H), 1.19 (t, 3H, J=7.0 Hz).

Sources & evidence

ORD record
ord-becfe2479a72483989d99d831dabcace
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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