Ammonium formate → Lenalidomide

HRID 1525634Notes

Reaction equation

HRID 1525634 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:19])[C:6]2=[O:11].C([O-])=O.[NH4+:23]>>[NH2:23][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:19])[C:6]2=[O:11]

Participants

3

Reactant 2

HCID 2723923Ammonium formateHCID 66823592HCID 66823592, compound

Product 1

HCID 216326LenalidomideYield 85%

Procedure

A mixture of 3-(4-chloro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-dioxopiperidine (5 g) in ammonium formate (30 ml) was stirred by heating up slowly to reflux and then reacted under ammonia for 6˜8 hours. The reaction mixture concentrated to dryness under reduced pressure. Recrystallization from heated isopropanol gave 3.96 g of target yield. yield: 85%. Purity: 99.17%. mp: 251.6˜253.9° C.

Workup

  1. temperatureby heating up slowly
  2. temperatureto reflux
  3. customreacted under ammonia for 6˜8 hours
  4. concentrationThe reaction mixture concentrated to dryness under reduced pressure
  5. customRecrystallization
  6. temperaturefrom heated isopropanol
  7. customgave 3.96 g of target
  8. customyield

Sources & evidence

ORD record
ord-fc3269c0361b4fde8976a100c8875a49
Source dataset
uspto-grants-2015_07
Patent number
US09085530B2

Reaction notes

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