Sodium Iodide → HCID 21418258, compound

HRID 441832Notes

Reaction equation

HRID 441832 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.Cl[CH2:21][CH2:22][CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(=O)C)C>[C:24]([CH2:23][CH2:22][CH2:21][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:25]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 123364-ChlorobutyronitrileHCID 203266297,7-Diphenyl-1,4-oxazepane

Product 1

HCID 21418258HCID 21418258, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

The mixture of 4.6 g of 7,7-diphenyl-hexahydro-1,4-oxazepine, 1.88 g of 4-chlorobutyronitrile, 1.88 g of anhydrous sodium carbonate, 0.3 g of sodium iodide and 60 ml of 2-methyl-4-pentanone is stirred at reflux for 23 hours and evaporated. The residue is partitioned between diethyl ether and water, the ethereal solution separated, washed with saturated aqueous sodium chloride, dried and evaporated, to give the 4-(3-cyanopropyl)-7,7-diphenyl-hexahydro-1,4-oxazepine melting at 89°-90°. (Analogously the 4-(4-cyanobutyl and 6-cyanohexyl)-7,7-diphenyl-hexahydro-1,4-oxazepines are prepared, melting at 67°-69° and showing an I.R. band at 2252cm-1 respectively).

Workup

  1. temperatureat reflux for 23 hours
  2. customevaporated
  3. customThe residue is partitioned between diethyl ether and water
  4. customthe ethereal solution separated
  5. washwashed with saturated aqueous sodium chloride
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-2bae4e14c42b4c3cbf84801d34ef504a
Source dataset
uspto-grants-1977_08
Patent number
US04042701

Reaction notes

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