Dicyclohexylcarbodiimide → N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2-methyl-6-(methyloxy)benzamide

HRID 20831

Reaction equation

HRID 20831 reaction equation
[NH2:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1([N:8]([CH3:10])[CH3:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.ClC1C(C(F)(F)F)=CC=CC=1C(NC(C1(N(C)C)CCCC1)C1C=CC=CC=1)=O.[CH3:46][O:47][C:48]1[CH:56]=[CH:55][CH:54]=[C:53]([CH3:57])[C:49]=1[C:50](O)=[O:51].O.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH3:9][N:8]([CH3:10])[C:3]1([CH:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:1][C:50](=[O:51])[C:49]2[C:48]([O:47][CH3:46])=[CH:56][CH:55]=[CH:54][C:53]=2[CH3:57])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 2731702-Methoxy-6-methylbenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 116115852-Chloro-N-[[1-(dimethylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide

Product 1

HCID 11588687N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2-methyl-6-(methyloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (0.220 g, 1 mmol), 2-methoxy-6-methylbenzoic acid (0.200 g, 1.2 mmol), 1-hydroxybenzotriazole hydrate (0.183 g, 1.2 mmol) and PS-DCC (1 g of 1.3 mmol/g loading, 1.3 mmol) in DCM (10 ml) was stirred vigorously overnight. The mixture was washed with saturated aqueous sodium hydrogen carbonate, the layers separated through a phase separation cartridge and the organic layer applied to an SCX cartridge. The cartridge was eluted with DCM (×2), and then methanol (×2) followed by 1M ammonia in methanol. Evaporation of the solvent afforded the title compound which was characterised. 1H NMR (CDCl3) δ: 1.00-1.10 (1H, m), 1.25-1.40 (1H, m), 1.40-1.60 (2H, m), 1.60-1.80 (2H, m), 1.80-2.00 (2H, m), 2.24 (6H, s), 2.28 (3H, s), 3.80 (3H, s), 5.17 (1H, d, J=6 Hz), 6.75 (1H, d, J=8 Hz), 6.79 (1H, d, J=8 Hz), 7.10 (1H, br s), 7.15-7.30 (4H, m), 7.44 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 367 (MH+). C23H30N2O2 requires 366. Ret. time 1.92 min. The title product was converted to the corresponding hydrochloride salt (0.34 g, 85%).

Workup

  1. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate
  2. customthe layers separated through a phase separation cartridge
  3. washThe cartridge was eluted with DCM (×2)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fdd1e5fac5a841df87c2ae73df0cbf53
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Linked notes

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