Triethylamine → HCID 10145374, compound

HRID 352440Notes

Reaction equation

HRID 352440 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 concentrated by evaporation 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 the solvent is eliminated in vacuo. The residue is chromatographed with methylene chloride/methanol 1:1 over silica gel. The fractions found to be uniform by 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 brownish-yellow oil, [α]D20=+35.1°

Workup

  1. concentrationThe mixture is concentrated by evaporation 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-96eb1e066c3349f486da4033b8d3ef49
Source dataset
uspto-grants-2004_06
Patent number
US06747044B2

Reaction notes

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