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Triethylamine → N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2-methyl-4,6-bis(trifluoromethyl)benzamide

HRID 20852
Notes
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Reaction equation

HRID 20852 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:3]=1[C:4](Cl)=[O:5].FC(F)(F)C1C=C(C(F)(F)F)C=CC=1C(OC)=O.[NH2:37][CH:38]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:39]1([N:44]([CH3:46])[CH3:45])[CH2:43][CH2:42][CH2:41][CH2:40]1.COC1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1C(NC(C1C=CC=CC=1)C(C)(N1CCCC1)CC)=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:45][N:44]([CH3:46])[C:39]1([CH:38]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[NH:37][C:4](=[O:5])[C:3]2[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:2]=2[CH3:1])[CH2:43][CH2:42][CH2:41][CH2:40]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 18925643Methyl 2,4-bis(trifluoromethyl)benzoateHCID 59347787HCID 59347787, compoundHCID 59347796(+/-)-2-(Methyloxy)-N-[2-methyl-1-phenyl-2-(1-pyrrolidinyl)butyl]-4,6-bis(trifluoromethyl)benzamide

Product 1

HCID 59347766
N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2-methyl-4,6-bis(trifluoromethyl)benzamide
Yield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methyl-4,6-bis(trifluoromethyl)benzoyl chloride and methyl 2,4-bis(trifluoromethyl)benzoate (approximately 0.5 mmol) prepared as described in D53 was dissolved in dry DCM (3 ml) and treated with (+)-{1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (109 mg, 0.50 mmol) and triethylamine (140 ul, 1.00 mmol) and left overnight at room temperature. The volatile components were removed under reduced pressure and the residue chromatographed on silica gel. Elution with 0-80% ethyl acetate in pentane gave the title product (86 mg, ca.36%). 1H NMR (CDCl3) δ: 0.95 (1H, br m), 1.44-1.86 (7H, overlapping m), 2.20 (6H, s), 2.41 (3H, br s), 5.10 (1H, d, J=5.6 Hz), 7.07 (1H, br s), 7.26-7.42 (5H, overlapping m), 7.67 (1H, s), 7.77 (1H, s). Mass Spectrum (Electrospray LC/MS): Found 473 (MH+) C24H26F6N2O requires 472. Ret time 2.25 min.

Workup

  1. customprepared
  2. customThe volatile components were removed under reduced pressure
  3. customthe residue chromatographed on silica gel
  4. washElution with 0-80% ethyl acetate in pentane

Sources & evidence

ORD record
ord-393535b390e64c34ba1549506cc2f4d3
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745642B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes