Triethylamine → N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-4-fluoro-2,6-dimethylbenzamide

HRID 20833Notes

Reaction equation

HRID 20833 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.C(N(CC)CC)C.[F:24][C:25]1[CH:33]=[C:32]([CH3:34])[C:28]([C:29](Cl)=[O:30])=[C:27]([CH3:35])[CH:26]=1>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:29](=[O:30])[C:28]2[C:27]([CH3:35])=[CH:26][C:25]([F:24])=[CH:33][C:32]=2[CH3:34])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 404271224-Fluoro-2,6-dimethylbenzoyl chloride

Product 1

HCID 59347804N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-4-fluoro-2,6-dimethylbenzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (0.904 g; 4.147 mmol) in DCM (45 ml) under argon at room temperature was added triethylamine (0.573 ml; 4.15 mmol), followed by a solution of 4-fluoro-2,6-dimethylbenzoyl chloride (0.773 g: 4.144 mmol) in DCM (5 ml). After 16 h. the reaction was washed with water, dried with MgSO4 and evaporated. The residue was chromatographed on silica gel eluting with an ethyl acetate-hexane 0 to 100% gradient to give the title compound (1.57 g; 100%). 1H NMR (CDCl3) δ: 0.85-1.00 (1H, m), 1.30-1.60 (3H, m), 1.60-1.75 (2H, m), 1.75-1.90 (2H, m), 2.22 (6H, s), 2.31 (6H, m), 5.18 (1H, d, J=6 Hz), 6.73 (2H, d, J=9.6 Hz overlaps 1H, br s), 7.20-7.35 (3H, m), 7.42 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 369 (MH+). C23H29FN2O requires 368. Ret. time 1.99 min. The free base was dissolved in methanol. 1M HCl/diethylether was added to the stirred solution and stirring continued at room temperature for 5 minutes. The solution was then evaporated under reduced pressure, redissolved in DCM and evaporated at reduced pressure. The resulting foam was dried for 16 hours at reduced pressure. The hydrochloride salt was obtained as a white foam (1.45 g).

Workup

  1. washAfter 16 h. the reaction was washed with water
  2. dry with materialdried with MgSO4
  3. customevaporated
  4. customThe residue was chromatographed on silica gel eluting with an ethyl acetate-hexane 0 to 100% gradient

Sources & evidence

ORD record
ord-8e82dc5b4c3c4bad93c1f5a521874a68
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

Loading…