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Diisopropylethylamine → Rac-2-chloro-n-(1-methyl-3-phenyl-piperidin-3-yl)-3-trifluoromethyl-benzamide

HRID 2177529
Notes
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Reaction equation

HRID 2177529 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:48][N:49]1[CH2:54][CH2:53][CH2:52][C:51]([NH2:61])([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:50]1>CN(C=O)C>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:61][C:51]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:52][CH2:53][CH2:54][N:49]([CH3:48])[CH2:50]1)=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59438412HCID 59438412, compound

Product 1

HCID 59438457Rac-2-chloro-n-(1-methyl-3-phenyl-piperidin-3-yl)-3-trifluoromethyl-benzamide
Yield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 33 mg (0.144 mmol) 2-chloro-3-(trifluoromethyl)benzoic acid (commercial), 75 mg (0.197 mmol) HATU and 90 ul (0.524 mmol) N-ethyldiisopropylamine in DMF (1 ml) was added a solution of 25 mg (0.131 mmol) rac-1-methyl-3-phenyl-piperidin-3-ylamine (Example A.1) in DMF (0.25 ml). The mixture was stirred at room temperature for 22 hours. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The solution was washed once with water and twice with a saturated sodium carbonate solution. The aqueous layer was extracted once with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 27 mg (52%) of the title compound as a light yellow oil. MS (m/e): MS (m/e): 397.2 (M+H)

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed once with water and twice with a saturated sodium carbonate solution
  4. extractionThe aqueous layer was extracted once with ethyl acetate
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-546d62d5f3524c35bfacd757be334532
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067911B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes