Hydrochloric Acid → HCID 18470687, compound

HRID 2228639Notes

Reaction equation

HRID 2228639 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:10](=[O:11])[N:9]([CH:12]3[C:18](=[O:19])[N:17](CO)[C:15](=[O:16])[CH2:14][CH2:13]3)[C:7](=[O:8])[C:5]=2[CH:6]=1.[C:22]1(=O)[O:27][C:25](=[O:26])[CH2:24][CH2:23]1.C(N(CC)CC)C.N1(C2C=CN=CC=2)CCCC1.Cl.C1C=CC2C(=O)N(C3[C:65](=[O:66])NC(=O)CC3)C(=O)C=2C=1.[OH2:67]>ClCCl.C(OCC)(=O)C>[O:8]=[C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10](=[O:11])[N:9]1[CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[N:17]([C:24]([C:25]([O:27][CH3:22])=[O:26])([CH3:23])[C:65]([OH:66])=[O:67])[C:18]1=[O:19]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 962Water2×HCID 5426ThalidomideHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 9900574145945-21-7

Product 1

HCID 18470687HCID 18470687, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.88 g (10 mmoles) N-hydroxymethylthalidomide, 2 g (20 mmoles) succinic anhydride, 2.8 ml (20 mmoles) triethylamine and 0.15 g (1 mmole) 4-pyrrolidinopyridine were stirred in 50 ml dry dichloromethane for 24 hours at room temperature. The reaction mixture was subsequently shaken firstly with 5% hydrochloric acid and then with water. After drying the organic phases over magnesium sulphate and removing the solvent by distillation, the residue obtained was treated with a small amount of ethyl acetate and the precipitated crystals were recrystallised from ethanol 2.66 g (68% theoretical) of compound 9 were obtained, with a melting point of 143 to 146° C. and a solubility in water of 16.7 mg/ml, corresponding to 11.1 mg thalidomide/ml.

Workup

  1. dry with materialAfter drying the organic phases over magnesium sulphate
  2. customremoving the solvent
  3. distillationby distillation
  4. customthe residue obtained
  5. customthe precipitated crystals were recrystallised from ethanol 2.66 g (68% theoretical) of compound 9
  6. customwere obtained, with a melting point of 143 to 146° C.

Sources & evidence

ORD record
ord-3c428310b8a6480a81b32c17b7a28c6e
Source dataset
uspto-grants-2002_07
Patent number
US06417197B1

Reaction notes

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