Ether hydrochloride → HCID 21988585, compound

HRID 448417Notes

Reaction equation

HRID 448417 reaction equation
[ClH:1].CCOCC.C(OC(=O)[NH:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17](=[O:34])[N:18]([C:25]1([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:19]2=[O:24])(C)(C)C>C(OCC)(=O)C>[ClH:1].[NH2:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17](=[O:34])[N:18]([C:25]1([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:19]2=[O:24]

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 67230396HCID 67230396, compound

Product 1

HCID 21988585HCID 21988585, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2N HCl/ether solution (8.5 mL) was added to a stirred solution of [2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-carbamic acid t-butyl ester (2.3 g, 5.7 mmol) in ethyl acetate (20 mL). The mixture was stirred at room temperature overnight. The mixture was filtered, and the solid was dried to gave 4-aminomethyl-2-(3-methyl-2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione hydrochloride (1.6 g, 80%) as a white solid: 1H NMR (DMSO-d6) δ 1.90 (s, 3H, CH3), 2.08 (m, 1H), 2.61-2.71 (m, 3H), 4.44 (M, 2H, CH2), 7.87-7.95 (m, 3H, Ar), 8.62 (s, 3H, NH3), 11.05 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.97, 28.52, 29.04, 36.98, 58.77, 123.14, 128.38, 131.10, 132.28, 134.64, 135.58, 167.31, 168.00, 171.93, 172.09.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solid was dried

Sources & evidence

ORD record
ord-7eb2db3e9704431da1b11fd656184d11
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

Loading…