Triethylamine → HCID 10145374, compound

HRID 1167589Notes

Reaction equation

HRID 1167589 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:12][CH2:13][CH2:14][OH:15])[CH:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:3][CH2:2]1.[F:16][C:17]([F:47])([F:46])[C:18]1[CH:19]=[C:20]([CH2:28][CH2:29][N:30]([CH3:45])[C:31](=[O:44])[C@H:32](OS(C)(=O)=O)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1.C(N(CC)CC)C>CC(C)=O>[F:16][C:17]([F:46])([F:47])[C:18]1[CH:19]=[C:20]([CH2:28][CH2:29][N:30]([CH3:45])[C:31](=[O:44])[C@@H:32]([N:9]2[CH2:10][CH2:11][CH:6]([N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH2:12][CH2:13][CH2:14][OH:15])[CH2:7][CH2:8]2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:21]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11469921HCID 11469921, compoundHCID 11488562HCID 11488562, compound

Product 1

HCID 10145374HCID 10145374, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.7 g of 4-[cyclopropylmethyl-(3-hydroxy-propyl)-amino]-piperidine are stirred together with 9.6 g of (R)-N-[2-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-2-methanesulphonyloxy-N-methyl-2-phenyl-acetamide (prepared from D-(−)-mandelic acid) and 3.4 ml of triethylamine in 200 ml of acetone for four hours at 65° C. The mixture is evaporated down in vacuo, combined with 100 ml of saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic fractions are dried over sodium sulphate and freed from solvent in vacuo. The residue is chromatographed with methylene chloride/methanol 1:1 over silica gel. The uniform fractions according to TLC are collected and the solvents are eliminated in vacuo. 5.5 g of (S)-N-[2-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-2-{4-[cyclopropylmethyl-(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. customThe mixture is evaporated down in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic fractions are dried over sodium sulphate
  4. customThe residue is chromatographed with methylene chloride/methanol 1:1 over silica gel
  5. customare collected

Sources & evidence

ORD record
ord-43824675209b4ce49beced3ba6c29acc
Source dataset
uspto-grants-2003_09
Patent number
US06620438B2

Reaction notes

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