Triethylamine → HCID 12019498, compound

HRID 352435Notes

Reaction equation

HRID 352435 reaction equation
Cl.Cl.[CH:3]1([CH2:6][N:7]([CH3:14])[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:5][CH2:4]1.[F:15][C:16]([F:46])([F:45])[C:17]1[CH:18]=[C:19]([CH2:27][CH2:28][N:29]([CH3:44])[C:30](=[O:43])[CH:31](OS(C)(=O)=O)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1.C(N(CC)CC)C>CC(C)=O.C(=O)([O-])O.[Na+]>[F:15][C:16]([F:45])([F:46])[C:17]1[CH:18]=[C:19]([CH2:27][CH2:28][N:29]([CH3:44])[C:30](=[O:43])[CH:31]([N:11]2[CH2:12][CH2:13][CH:8]([N:7]([CH2:6][CH:3]3[CH2:4][CH2:5]3)[CH3:14])[CH2:9][CH2:10]2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:20]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12019500HCID 12019500, compoundHCID 22712050HCID 22712050, compound

Product 1

HCID 12019498HCID 12019498, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

11.9 g of 4-(cyclopropylmethyl-methyl-amino)-piperidine-dihydrochloride are taken up in 400 ml of acetone and combined with 21.7 g of N-[2-(3.5-bis-trifluoromethyl-phenyl)-ethyl]-2-methanesulphonyloxy-N-methyl-2-phenyl-acetamide and 21 ml of triethylamine. The mixture is refluxed for 16 hours, then the solvent is eliminated in vacuo and the residue is taken up in 10% sodium hydrogen carbonate solution. It is extracted with ether, the combined organic phases are dried over sodium sulphate and the solvent is eliminated in vacuo. The residue is filtered with ethyl acetate/methanol/conc. ammonia solution 70:30:1 through silica gel, freed from the solvents in vacuo and crystallised in methanol with fumaric acid. The precipitate is suction filtered, washed with methanol and dried in vacuo. 9.3 g of N-[2-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-2-[4-(cyclopropylmethyl-methyl-amino)-piperidin-1-yl]-N-methyl-2-phenyl-acetamide are obtained as the sesquifumarate.

Workup

  1. temperatureThe mixture is refluxed for 16 hours
  2. extractionIt is extracted with ether
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. filtrationThe residue is filtered with ethyl acetate/methanol/conc
  5. customcrystallised in methanol with fumaric acid
  6. filtrationfiltered
  7. washwashed with methanol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1f03a76eacbb44659443541adbeb8caa
Source dataset
uspto-grants-2004_06
Patent number
US06747044B2

Reaction notes

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