Gabapentin → HCID 68517401, compound

HRID 1988865Notes

Reaction equation

HRID 1988865 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[C:11]([O:14]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.C(N(C(C)C)CC)(C)C.[NH2:31][CH2:32][C:33]1([CH2:39][C:40]([OH:42])=[O:41])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C(Cl)Cl.CCl.CN(C)C=O.C(OCC)(=O)C>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:11]([NH:31][CH2:32][C:33]1([CH2:39][C:40]([OH:42])=[O:41])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:14]

Participants

9

Reactant 4

HCID 3446GabapentinHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 137401503-(Bromomethyl)phenol

Product 1

HCID 68517401HCID 68517401, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6327Methyl ChlorideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-bromomethylphenol (0.50 g, 2.67 mmol) in methylene chloride (8 ml), bis(trichloromethyl)carbonate (triphosgene, 0.368 g, 1.24 mmol) dissolved in methyl chloride (2 ml) and diisopropylethylamine (0.466 ml, 2.67 mmol) were cool added. The solution thus obtained was stirred one night at room temperature and then refluxed for 2 hours, This cooled solution was then dropped in a suspension of 1-(aminomethyl)cyclohexaneacetic acid (gabapentin, 0.911 g, 5.35 mmol) and diisopropylethylamine (0.932 ml, 5.35 mmol) in anhydrous dimethylformamide (4 ml). After 3 hours stirring, to the mixture ethyl acetate was added and it was washed with a 4% hydrochloric acid solution. The organic phase was dried under vacuum and the raw product thus obtained was purified by silica gel chromatography with n-hexane/ethyl acetate 1/1 (v/v) as eluent. The desired product was obtained as an oil (0.100 g) that was employed without further purification.

Workup

  1. additionadded
  2. customThe solution thus obtained
  3. temperaturerefluxed for 2 hours
  4. additionwas added
  5. washit was washed with a 4% hydrochloric acid solution
  6. customThe organic phase was dried under vacuum
  7. customthe raw product thus obtained
  8. customwas purified by silica gel chromatography with n-hexane/ethyl acetate 1/1 (v/v) as eluent

Sources & evidence

ORD record
ord-c89744d486844a2f86527539e6f92f96
Source dataset
uspto-grants-2010_01
Patent number
US07642289B2

Reaction notes

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