Triethylamine → HCID 12019498, compound

HRID 2121288Notes

Reaction equation

HRID 2121288 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 freed from solvent in vacuo. The residue is filtered with ethyl acetate/methanol/conc. ammonia solution 70:30:1 over silica gel, freed from the solvents in vacuo and brought to crystallisation 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. custombrought to crystallisation in methanol with fumaric acid
  6. filtrationfiltered
  7. washwashed with methanol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-62fd8de3dfdd4140a835b4161c0211f8
Source dataset
uspto-grants-2004_02
Patent number
US06696042B2

Reaction notes

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