Triethylamine → 4-[2-(4-Ethyl-phenyl)-ethylcarbamoyl]-4-(2-fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 730199Notes

Reaction equation

HRID 730199 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.[CH2:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH2:38])=[CH:32][CH:31]=1)[CH3:29].[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][C:49]([CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=2[F:62])([C:52](O)=[O:53])[CH2:48][CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40].C(N(CC)CC)C>O1CCCC1.C(OCC)C>[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][C:49]([C:52](=[O:53])[NH:38][CH2:37][CH2:36][C:33]2[CH:34]=[CH:35][C:30]([CH2:28][CH3:29])=[CH:31][CH:32]=2)([CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=2[F:62])[CH2:48][CH2:47]1)=[O:45])([CH3:41])([CH3:42])[CH3:40]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1440474-EthylphenethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 236005311-(tert-Butoxycarbonyl)-4-(2-fluorobenzyl)piperidine-4-carboxylic acid

Product 1

HCID 236010764-[2-(4-Ethyl-phenyl)-ethylcarbamoyl]-4-(2-fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl esterYield 65.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.650 g, 1.47 mmol) was added to a solution of 2-(4-ethyl-phenyl)-ethylamine (0.235 mL, 1.47 mmol), 4-(2-fluoro-benzyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (0.330 g, 0.978 mmol) and triethylamine (0.409 mL, 2.93 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 to give 0.301 g (65 %) of 4-[2-(4-ethyl-phenyl)-ethylcarbamoyl]-4-(2-fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester. LRMS m/z 469.1 (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

Sources & evidence

ORD record
ord-569bf31ad5034c63a808bbf2bcb87280
Source dataset
uspto-grants-2009_09
Patent number
US07582654B2

Reaction notes

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