Triethylamine → HCID 22712057, compound

HRID 2121291Notes

Reaction equation

HRID 2121291 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:11][CH2:12][CH2:13][OH:14])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]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.C(=O)([O-])O.[Na+]>CC(C)=O>[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:8]2[CH2:7][CH2:6][CH:5]([N:4]([CH2:3][CH2:2][OH:1])[CH2:11][CH2:12][CH2:13][OH:14])[CH2:10][CH2:9]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 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 12019500HCID 12019500, compoundHCID 22712053HCID 22712053, compound

Product 1

HCID 22712057HCID 22712057, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.4 g of the oil of 4-[(2-hydroxy-ethyl)-(3-hydroxy-propyl)-amino]-piperidine prepared according to b) are taken up in 300 ml of acetone, combined with 13.8 g of N-[2-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-2-methanesulphonyloxy-N-methyl-2-phenyl-acetamide and 33 ml of triethylamine and refluxed for 6 hours. The mixture is cooled, the solvent is eliminated in vacuo, the residue is stirred into 10% sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate, the solvent is eliminated in vacuo and the residue is chromatographed over silica gel with ethyl acetate/methanol/conc. ammonia solution 20:80:1. The uniform fractions according to TLC are combined and freed from the solvents in vacuo. 8.4 g of N-[2-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-2-{4-[(2-hydroxy-ethyl)-(3-hydroxy-propyl)-amino]-piperidin-1-yl}-N-methyl-2-phenyl-acetamide are obtained as a yellowish-brown oil.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customthe residue is chromatographed over silica gel with ethyl acetate/methanol/conc

Sources & evidence

ORD record
ord-fde635699190460899709574739a1e25
Source dataset
uspto-grants-2004_02
Patent number
US06696042B2

Reaction notes

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