Triethylamine → HCID 22712057, compound

HRID 1167587Notes

Reaction equation

HRID 1167587 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-e93bd00dda5d41a3b62a07f4247400af
Source dataset
uspto-grants-2003_09
Patent number
US06620438B2

Reaction notes

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