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

HRID 20845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20845
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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 59347772(+/-)-N-[(1-aminocyclopentyl)(phenyl)methyl]-2,6-dimethylbenzamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b1fb220a6ee241009edb0a778260bc95
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745642B2

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