Methylamine → HCID 59296034, compound

HRID 2233379Notes

Reaction equation

HRID 2233379 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@@:13]([OH:27])([CH3:26])[CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:8][CH2:7]1.CN>C(O)C.CO>[NH2:15][CH2:14][C@@:13]([CH3:26])([OH:27])[CH2:12][N:9]1[CH2:10][CH2:11][CH:6]([O:5][C:4]2[CH:28]=[CH:29][C:30]([Cl:31])=[C:2]([Cl:1])[CH:3]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 59296070HCID 59296070, compound

Product 1

HCID 59296034HCID 59296034, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-[(2S)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxy-2-methylpropyl]-1H-isoindole-1,3(2H)-dione (278 mg, 0.6 mmoles) in ethanol (5 ml) was added aqueous methylamine (40% wt. solution in water, 6 ml). The mixture was stirred at room temperature for 24 h and then concentrated in vacuo to leave a crude yellow glass. This glass was dissolved in methanol (2 ml), added to an Isolute Flash SCX cartridge (2 g), washed with methanol (25 ml) and 7N ammonia in methanol (25 ml). The methanolic ammonia was concentrated in vacuo to give the title compound as a yellow glass (165 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customto leave a crude yellow glass
  3. additionadded to an Isolute Flash SCX cartridge (2 g)
  4. washwashed with methanol (25 ml) and 7N ammonia in methanol (25 ml)
  5. concentrationThe methanolic ammonia was concentrated in vacuo

Sources & evidence

ORD record
ord-35d24192c8c6423897fa9ab9d0a05791
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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