Triethylamine → HCID 11637840, compound

HRID 853171Notes

Reaction equation

HRID 853171 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:25][N:26]=[C:27]=[O:28]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:27](=[O:28])[NH:26][CH3:25])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 887902Safinamide Impurity 8

Product 1

HCID 11637840HCID 11637840, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a sealed glass tube, a solution of 1.0 g of [4-(3-fluoro-benzyloxy)-phenyl]-methanol [Example 25b)], 0.03 ml of triethylamine and 0.245 g of methyl isocyanate in 40 ml of dichloromethane was heated at 40° C. for 3 d. At that time a transformation rate of 50% was reached, determined by NMR. For the working-up, the reaction mixture was cooled and evaporated. The residue was dissolved in 2 ml of pyridine and 1 ml of acetic acid anhydride and the solution stirred at room temperature for 3 h. Thereafter, the mixture was evaporated under reduced pressure. For purification, the crude material obtained was chromatographed on silica gel using a 2:1-mixture of heptane and ethyl acetate as the eluent. There were obtained 580 mg (47% of theory) of methyl-carbamic acid 4-(3-fluoro-benzyloxy)-benzyl ester as a white solid; MS: m/e=289 (M)+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customevaporated
  3. dissolutionThe residue was dissolved in 2 ml of pyridine
  4. customThereafter, the mixture was evaporated under reduced pressure
  5. customFor purification
  6. customthe crude material obtained
  7. customwas chromatographed on silica gel using a 2

Sources & evidence

ORD record
ord-6725ba31080843df94a4de13932c315f
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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