2-(3-Oxobutyl)isoindoline-1,3-dione → 3-{4-[2-(4-Methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine

HRID 1726252Notes

Reaction equation

HRID 1726252 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.O=[C:34]([CH3:48])[CH2:35][CH2:36][N:37]1C(=O)C2C(=CC=CC=2)C1=O>>[CH3:32][S:29]([C:26]1[CH:27]=[CH:28][C:23]([C:14]2([CH:11]3[CH2:10][CH2:9][N:8]([CH:34]([CH3:48])[CH2:35][CH2:36][NH2:37])[CH2:13][CH2:12]3)[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15]2)=[CH:24][CH:25]=1)(=[O:31])=[O:30]

Participants

3

Reactant 2

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 689706894-[2-(4-Methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689687073-{4-[2-(4-Methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine

Procedure

Using general procedure C with the above carbamate (170 mg, 0.37 mmol), then using general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (70 mg, 0.32 mmol) followed by general procedure D gave 3-{4-[2-(4-methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine as a white solid (46 mg, 68% over 3 steps).

Sources & evidence

ORD record
ord-eeefd997afd54942b83d26732f0e8031
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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