Dimethylformamide → (+/-)-4-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl) amino]-butanenitrile

HRID 55372

Reaktionsgleichung

Reaktionsgleichung von HRID 55372
[C:1]1([CH2:7][NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[O:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][C:24]#[N:25].CN(C)C=O>C(N(CC)CC)C>[O:11]1[C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][CH2:15][CH:10]1[CH2:9][N:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:21][CH2:22][CH2:23][C:24]#[N:25]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 214124-BromobutyronitrileHCID 10753388Benzyl-chroman-2-ylmethyl-amine; oxalic acid

Produkt 1

HCID 21460889(+/-)-4-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl) amino]-butanenitrileAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 12.5 g of 3,4-dihydro-N-(phenylmethyl)-2H-1-benzopyran-2-methanamine, 9 g of 4-bromobutanenitrile, 200 ml of N,N-dimethylformamide and 10 ml of N,N-diethylethanamine was stirred for 72 hour at room temperature. The reaction mixture was evaporated and the residue was partitioned between 1,1'-oxybisethane and water. The organic layer was separated, dried, filtered and evaporated, yielding 11 g (68.7%) of (±)-4-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl) amino]-butanenitrile (interm. 53).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between 1,1'-oxybisethane and water
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f31c99b19d4442d2a302c1cf4cb988b9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624952

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