Triethylamine → HCID 22712057, compound

HRID 352438Notes

Reaction equation

HRID 352438 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>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: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 3

HCID 8471TriethylamineHCID 12019500HCID 12019500, compoundHCID 22712053HCID 22712053, compound

Product 1

HCID 22712057HCID 22712057, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

6.4 g of the oil of 4-[(2-hydroxy-ethyl)-(3-hydroxy-propyl)-amino]-piperidine prepared in 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 in 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 with ethyl acetate/methanol/conc. ammonia solution 20:80:1 over silica gel. The fractions found to be uniform by 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; [α]D20=+29.6°.

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 with ethyl acetate/methanol/conc

Sources & evidence

ORD record
ord-a283af68afed436eae33ec370fe461d7
Source dataset
uspto-grants-2004_06
Patent number
US06747044B2

Reaction notes

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