(+)-N-[{1-[bis(phenylmethyl)amino]cyclopentyl}(phenyl)methyl]-2,6-dimethylbenzamide → HCID 59347772, compound

HRID 20845Notes

Reaction equation

HRID 20845 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[C:9]2([CH:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:15][C:16](=[O:25])[C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:24])[CH2:13][CH2:12][CH2:11][CH2:10]2)C=CC=CC=1>[Pd].[C].C(O)C>[NH2:8][C:9]1([CH:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:15][C:16](=[O:25])[C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:24])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 59347832(+)-N-[{1-[bis(phenylmethyl)amino]cyclopentyl}(phenyl)methyl]-2,6-dimethylbenzamide

Product 1

HCID 59347772HCID 59347772, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

The title compound (1.14 g; 71%) was prepared from the catalytic hydrogenation of (±)-N-[{1-[bis(phenylmethyl)amino]cyclopentyl}(phenyl)methyl]-2,6-dimethylbenzamide D34 (2.51 g; 5 mmol) over 10% Pd/Carbon (0.4 g) in 3 MHCl (8 ml) and ethanol (150 ml) in a similar manner to that described in D29. The ethanol was evaporated off in vacuo and the residual material was partitioned between DCM and sodium bicarbonate solution and dried (Na2SO4). The filtrate was reduced in volume by evaporation in vacuo and loaded onto an SCX cartridge. Washing with DCM, then methanol followed by elution with 1M ammonia in methanol afforded the title product (90 mg, 88%). 1H NMR (CDCl3) δ: 0.98-1.96 (10H, m). 2.23 (6H, s), 4.97 (1H, m), 7.0 (2H, m), 7.16 (1H, m), 7.22-7.41 (6H, m); Mass Spectrum (Electrospray LC/MS). Found 323 (MH+). C21H26N2O requires 322. Ret. time 1.69 min.

Workup

  1. customThe ethanol was evaporated off in vacuo
  2. customthe residual material was partitioned between DCM and sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customThe filtrate was reduced in volume by evaporation in vacuo
  5. washWashing with DCM
  6. washmethanol followed by elution with 1M ammonia in methanol

Sources & evidence

ORD record
ord-b1fb220a6ee241009edb0a778260bc95
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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