Water → HCID 20326670, compound

HRID 1288561Notes

Reaction equation

HRID 1288561 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][C:28]#[N:29].O>CN(C)C=O>[C:28]([CH2:27][N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:13][CH2:12][CH2:11]1)#[N:29]

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 203266297,7-Diphenyl-1,4-oxazepane

Product 1

HCID 20326670HCID 20326670, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the solution of 2.5 g of 7,7-diphenyl-hexahydro-1,4-oxazepine in 5 ml of dimethylformamide, 1.5 g of anhydrous potassium carbonate are added while stirring, followed by the dropwise addition of the solution of 0.85 g of chloroacetonitrile in 2 ml of dimethylformamide and the suspension is stirred for 5 hours at room temperature. It is poured onto a mixture of ice and water, the aqueous phase extracted twice with 20 ml of diethyl ether each, the extract dried, filtered and evaporated. The residue is recrystallized from ethanol, to yield the 4-cyanomethyl-7,7-diphenyl-hexahydro-1,4-oxazepine melting at 119°-121° (its hydrochloride melts at 178°-180° with decomposition).

Workup

  1. stirringthe suspension is stirred for 5 hours at room temperature
  2. extractionthe aqueous phase extracted twice with 20 ml of diethyl ether each, the extract
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-73b40cb4cfc34f9b9a9fbef44b31da12
Source dataset
uspto-grants-1976_10
Patent number
US03988448

Reaction notes

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