Triethylamine → Lenalidomide

HRID 1843450Notes

Reaction equation

HRID 1843450 reaction equation
[CH2:1]1[CH:8]([N:9]2[C:13](=[O:14])[C:12]3[CH:15]=[CH:16][CH:17]=[C:18]([NH2:19])[C:11]=3[CH2:10]2)[C:6](=[O:7])[NH:5][C:3](=[O:4])[CH2:2]1.Cl.C(N(CC)CC)C>CO>[NH2:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:12]2[C:11]=1[CH2:10][N:9]([CH:8]1[CH2:1][CH2:2][C:3](=[O:4])[NH:5][C:6]1=[O:7])[C:13]2=[O:14]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 44234581CC 5013 hydrochloride

Product 1

HCID 216326Lenalidomide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
7.5 °C

Procedure

The lenalidomide hydrochloride salt was suspended in methanol (350 ml) and 1.1 mole equivalent of triethylamine was slowly added whilst stirring. The reaction mixture was stirred at ambient temperature for the next 45 minutes and then cooled at 5-10° C. and maintained at the same temperature for the next 45 minutes. The precipitated solid was filtered and dried. It was then washed with methanol (105 ml) and the resultant lenalidomide isolated by filtration. The pure product was dried at 50-55° C. and 150-200 mmHg pressure for about 7-8 hours.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for the next 45 minutes
  2. temperaturemaintained at the same temperature for the next 45 minutes
  3. filtrationThe precipitated solid was filtered
  4. customdried
  5. washIt was then washed with methanol (105 ml)

Sources & evidence

ORD record
ord-d30016703a354024900252e9ab2f34e8
Source dataset
uspto-grants-2015_02
Patent number
US08946265B2

Reaction notes

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