Sulfuric Acid → HCID 20326662, compound

HRID 1288558Notes

Reaction equation

HRID 1288558 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][CH2:7][CH2:6]1)#[N:2].[Cl-:24].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>C(OCC)C.O>[ClH:24].[ClH:24].[NH2:2][CH2:1][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6451240Aluminum(III) ChlorideHCID 20326631HCID 20326631, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20326662HCID 20326662, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3.06 g of 4-(2-cyanoethyl)-7,7-diphenyl-hexahydro-1,4-oxazepine are added portionwise to the suspension prepared by combining the solution of 1.33 g of anhydrous aluminum chloride in 30 ml of diethyl ether with that of 0.38 g of lithium aluminum hydride in 30 ml of diethyl ether while stirring and cooling with an ice-bath. The mixture is allowed to warm up to room temperature, stirred for 51/2 hours and cooled again to 0°-5°. Thereupon 5 ml of water and 15 ml of 3N aqueous sulfuric acid are added and the organic layer extracted with 3N aqueous sulfuric acid. The aqueous layers are combined, made basic with concentrated aqueous sodium hydroxide and the mixture extracted four times with 15 ml of diethyl ether each. The extract is dried, filtered and evaporated. The residue is taken up in ethanol and the solution acidified with ethereal hydrogen chloride, to yield the 4-(3-aminopropyl)-7,7-diphenyl-hexahydro-1,4-oxazepine dihydrochloride melting at 190°-192° with decomposition.

Workup

  1. customprepared
  2. temperaturecooling with an ice-bath
  3. stirringstirred for 51/2 hours
  4. temperaturecooled again to 0°-5°
  5. extractionthe organic layer extracted with 3N aqueous sulfuric acid
  6. extractionthe mixture extracted four times with 15 ml of diethyl ether each
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e79bb6f1d6744ad99b5d044652d940b4
Source dataset
uspto-grants-1976_10
Patent number
US03988448

Reaction notes

Loading…