Triethylamine → HCID 22240552, compound

HRID 892267Notes

Reaction equation

HRID 892267 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][NH:37][C:38](=[O:52])[CH2:39][C:40]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[F:53][C:54]1[CH:59]=[CH:58][C:57]([CH2:60][CH2:61][C:62](O)=[O:63])=[CH:56][CH:55]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][NH:37][C:38](=[O:52])[CH2:39][C:40]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:45][CH2:44][N:43]([C:62](=[O:63])[CH2:61][CH2:60][C:57]2[CH:58]=[CH:59][C:54]([F:53])=[CH:55][CH:56]=2)[CH2:42][CH2:41]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1363023-(4-Fluorophenyl)propionic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22240781HCID 22240781, compound

Product 1

HCID 22240552HCID 22240552, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.311 g, 0.704 mmol) was added to a solution of N-[2-(2-fluoro-phenyl)-ethyl]-2-(4-phenyl-piperidin-4-yl)-acetamide (0.200 g, 0.587 mmol), 3-(4-Fluoro-phenyl)-propionic acid (0.118 g, 0.704 mmol) and triethylamine (0.245 mL, 1.76 mmol) in tetrahydrofuran (5 mL). After 1 hour the mixture was diluted with ethyl ether (20 mL) and washed with saturated aqueous sodium bicarbonate (20 mL) followed by water (2×10 mL). The organic layer was collected, concentrated under reduced pressure and crude product purified by column chromatography on silica gel to give 0.098 g (34%) of N-[2-(2-fluoro-phenyl)-ethyl]-2-{1-[3-(4-fluoro-phenyl)-propionyl]-4-phenyl-piperidin-4-yl}-acetamide. LRMS m/z 491.1 (M+H)+.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (20 mL)
  2. customThe organic layer was collected
  3. concentrationconcentrated under reduced pressure and crude product
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b97de14bd04042ccb00523729691140f
Source dataset
uspto-grants-2006_02
Patent number
US07005436B2

Reaction notes

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