2-(3-Oxobutyl)isoindoline-1,3-dione → [1-(3-Amino-1-methylpropyl)-piperidin-4-yl]-benzyl-(4-methoxy-phenyl)-amine

HRID 1726153Notes

Reaction equation

HRID 1726153 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O=[C:31]([CH3:45])[CH2:32][CH2:33][N:34]1C(=O)C2C(=CC=CC=2)C1=O>>[NH2:34][CH2:33][CH2:32][CH:31]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)[CH3:45]

Participants

3

Reactant 2

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 689700134-[Benzyl-(4-methoxyphenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68972467[1-(3-Amino-1-methylpropyl)-piperidin-4-yl]-benzyl-(4-methoxy-phenyl)-amine

Procedure

Using general procedure C with the above carbamate (303 mg, 0.765 mmol), then general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (320 mg, 1.47 mmol) and then using general procedure D gave [1-(3-amino-1-methylpropyl)-piperidin-4-yl]-benzyl-(4-methoxy-phenyl)-amine as a colorless oil (190 mg, 68% over 3 steps).

Sources & evidence

ORD record
ord-cece953307a74e6c9c1d07de1646d741
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

Loading…