Dichloromethane → 4-[2-(acetylamino)phenyl]-1,3-dihydro-1-[1-(phenylmethyl)-4-piperidinyl]-2H-benzimidazol-2-one

HRID 1699252

Reaktionsgleichung

Reaktionsgleichung von HRID 1699252
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CCN([CH:21]([CH3:23])[CH3:22])C(C)C.[C:24]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](=O)[CH2:35]Br)(=[O:26])[CH3:25].[O-:38][C:39]#[N:40].[Na+].Cl[CH2:43]Cl>C(OCC)(=O)C.CO.C(O)(=O)C>[C:24]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[C:35]2[NH:40][C:39](=[O:38])[N:1]([CH:2]3[CH2:7][CH2:6][N:5]([CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH2:4][CH2:3]3)[C:22]=2[CH:21]=[CH:23][CH:43]=1)(=[O:26])[CH3:25]

Komponenten

8

Edukt 5

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 517096Sodium CyanateHCID 2749459N-[2-(2-bromoacetyl)phenyl]acetamide

Produkt 1

HCID 183211834-[2-(acetylamino)phenyl]-1,3-dihydro-1-[1-(phenylmethyl)-4-piperidinyl]-2H-benzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

To a solution of 26.3 g (0.138 mol) of 4-amino1-(phenylmethyl)piperidine and 17.8 g (0.138 mol) of DIEA in 300 ml of dichloromethane was added dropwise a solution of 35.4 g (0.138 mol) of 1-[2-(acetylamino)phenyl]-2-bromoethanone in 150 ml of dichloromethane and the mixture was kept for a further 2 hours at room temperature. With external cooling with ice 13.5 g (0.20 mol) of sodium cyanate and 12 ml of glacial acetic acid were then added and the mixture was stirred overnight in a thawing ice bath. It was washed with water and saturated sodium hydrogen carbonate solution, dried over sodium sulphate and freed from solvent. The residue was triturated with 50 ml of ethyl acetate-methanol mixture (9/1 v/v), the resulting crystals were suction filtered, washed with ethyl acetate and dried in vacuo. 37.0 g (68.7% of theory) of colourless crystals were obtained, Rf=0.41 (eluant: dichloromethane/methanol 9/1 v/v)

Aufarbeitung

  1. additionwere then added
  2. washIt was washed with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulphate
  4. customThe residue was triturated with 50 ml of ethyl acetate-methanol mixture (9/1 v/v)
  5. filtrationfiltered
  6. washwashed with ethyl acetate
  7. customdried in vacuo
  8. custom37.0 g (68.7% of theory) of colourless crystals were obtained

Quellen und Nachweise

ORD-Eintrag
ord-69ab09b5839d4e70b3f79e36663201ca
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344449B1

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