Aminoacetonitrile → (10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-yl)methyl-(cyanomethyl)carbamate

HRID 648562Notes

Reaction equation

HRID 648562 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6](=[O:18])[N:7]2[C:12]=1[C:11]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:10]=1[CH2:9][CH2:8]2.Cl[C:26](OC1C=CC=CC=1)=[O:27].[NH2:35][CH2:36][C:37]#[N:38].C(=O)([O-])[O-]>O1CCOCC1.N1C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[CH:16][C:10]2[CH2:9][CH2:8][N:7]3[C:12](=[C:3]([CH2:2][NH:38][CH2:37][C:36]#[N:35])[CH:4]=[C:5]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:6]3=[O:18])[C:11]=2[CH:13]=1.[Cl:17][C:14]1[CH:15]=[CH:16][C:10]2[CH2:9][CH2:8][N:7]3[C:12](=[C:3]([CH2:2][O:1][C:26](=[O:27])[NH:38][CH2:37][C:36]#[N:35])[CH:4]=[C:5]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:6]3=[O:18])[C:11]=2[CH:13]=1

Participants

8

Reactant 4

HCID 10901AminoacetonitrileHCID 15891Phenyl chloroformateHCID 19660Carbonate IonHCID 147701266,7-dihydro-1-(hydroxymethyl)-3-phenyl-10-chloro-4H-benzo[a]quinolizine-4-one

Product 2

HCID 14770161(10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-yl)methyl-(cyanomethyl)carbamateHCID 14770162[[(10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-yl)methyl]amino]acetonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 0.676 g of 6,7-dihydro-1-(hydroxymethyl)-3-phenyl-10-chloro-4H-benzo[a]quinolizine-4-one in 18 ml of dioxane was treated with 0.6 ml of phenyl chloroformate and 0.42 ml of pyridine and stirred at room temperature for 3 hours. 1.03 g of aminoacetonitrile were then added and the mixture was stirred at 100° until carbonate was no longer present according to thin-layer chromatography. After evaporation, the residue was taken up in chloroform, washed twice with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. Chromatography over silica gel [elution agent toluene/dioxane (9:1)] gave [[(10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-yl)methyl]amino]acetonitrile of m.p. 181°-183° (from methanol) as well as in a second fraction (10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-yl)methyl-(cyanomethyl)carbamate of m.p. 166°-167° (from toluene).

Workup

  1. customAfter evaporation
  2. washwashed twice with water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8eb3d96fc83c4df582a5d58d7db02bf1
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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