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Triethylamine → HCID 59347826, compound

HRID 20848
Notes
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Reaction equation

HRID 20848 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.[CH3:37][C:38]([N:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1)([CH3:47])[CH:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(CC)CC)C>C(Cl)Cl>[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]([NH:46][CH:39]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:38]([CH3:47])([N:48]1[CH2:49][CH2:50][CH2:51][CH2:52]1)[CH3:37])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 18925643Methyl 2,4-bis(trifluoromethyl)benzoateHCID 25158607[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amineHCID 59347787HCID 59347787, compound

Product 1

HCID 59347826HCID 59347826, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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 (+)-[2-methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amine D6 (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 as an gum (127 mg, ca.54%). 1H NMR (CDCl3) δ: 0.90 (3H, s), 1.01 (3H, s), 1.70 (4H, overlapping m), 2.47 (3H, s), 2.63 (4H, overlapping m), 4.84 (1H, d, J=2.8 Hz), 7.16 (1H, br s), 7.26-7.38 (5H, overlapping m) 7.67 (1H, s), 7.77 (1H, s). Mass Spectrum (Electrospray LC/MS): Found 473 (MH+) C24H26F6N2O requires 472. Ret time 2.24 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-1f3ef1c572cb429291e3365c23bc86fb
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