Triethylamine → HCID 59596848, compound

HRID 1261444Notes

Reaction equation

HRID 1261444 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)=[CH:9][C:8]=1[O:20][CH3:21].C(N(CC)CC)C.[CH3:32][O:33][C:34](=[O:37])[CH2:35]Br>C(#N)C>[CH3:32][O:33][C:34](=[O:37])[CH2:35][N:15]([CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]2[CH:22]=[CH:23][CH:24]=[C:2]([F:1])[CH:3]=2)=[C:8]([O:20][CH3:21])[CH:9]=1)[CH2:16][CH:17]1[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 59596839HCID 59596839, compound

Product 1

HCID 59596848HCID 59596848, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.271 g (0.82 mmol) of [2-[4-(3-fluoro-benzyloxy)-3-methoxy-phenyl]-ethyl]-(cyclopropylmethyl)amine, 0.140 ml (1 mmol) of triethylamine and 0.155 g (0.89 mmol) of bromo-acetic acid methyl ester were dissolved in 5 ml of acetonitrile and the reaction was carried out at 70° C. overnight. Solvent was removed under vacuum, water was added to the residue and the product was extracted with ethyl acetate. The crude product was purified by flash chromatography (hexane/ethyl acetate 100:0→80:20 gradient v:v) and 0.32 g (97% yield) of the title compound was isolated as a yellow oil.

Workup

  1. customSolvent was removed under vacuum, water
  2. additionwas added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. customThe crude product was purified by flash chromatography (hexane/ethyl acetate 100:0→80:20 gradient v:v)

Sources & evidence

ORD record
ord-e026e35ecccb41ebb0c512b8c621ceef
Source dataset
uspto-grants-2013_06
Patent number
US08470877B2

Reaction notes

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