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Diisopropylethylamine → 1-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic Acid 2-methyl-4-[methyl-(4-trifluoromethyl-phenyl)-carbamoyl]-benzylamide

HRID 220981
Notes
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Reaction equation

HRID 220981 reaction equation
C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]([CH3:39])([CH3:38])[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH:32]([C:35]([OH:37])=O)[CH2:31][CH2:30]1.[NH2:40][CH2:41][C:42]1[CH:61]=[CH:60][C:45]([C:46]([N:48]([CH3:59])[C:49]2[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:57])[F:56])=[CH:51][CH:50]=2)=[O:47])=[CH:44][C:43]=1[CH3:62].CCN(C(C)C)C(C)C>ClCCl>[CH3:62][C:43]1[CH:44]=[C:45]([C:46](=[O:47])[N:48]([CH3:59])[C:49]2[CH:54]=[CH:53][C:52]([C:55]([F:56])([F:57])[F:58])=[CH:51][CH:50]=2)[CH:60]=[CH:61][C:42]=1[CH2:41][NH:40][C:35]([CH:32]1[CH2:31][CH2:30][N:29]([CH2:28][CH2:27][C:26]([CH3:25])([CH3:39])[CH3:38])[CH2:34][CH2:33]1)=[O:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 231123781-(3,3-Dimethylbutyl)piperidine-4-carboxylic acidHCID 575553064-Aminomethyl-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamide

Product 1

HCID 575554091-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic Acid 2-methyl-4-[methyl-(4-trifluoromethyl-phenyl)-carbamoyl]-benzylamide
Yield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PyBroP (188 mg, 0.40 mmol) and 1-(3,3-dimethyl-butyl)-piperidine-4-carboxylic acid (82 mg, 0.38 mmol) were added to a solution of 4-aminomethyl-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamide from Example E118.3 (100 mg, 0.31 mmol) in dichloromethane (5 ml) and DIEA (0.081 ml, 0.46 mmol). The mixture was stirred at room temperature for 2 days, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a off-white powder identified as the title compound (22 mg, 14%).

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialbrine, dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
  5. customto give a off-white powder

Sources & evidence

ORD record
ord-53ac1381c0744c34a8dc00e073105788
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202858B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes