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Sulfuric Acid → HCID 20326662, compound

HRID 372797
Notes
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Reaction equation

HRID 372797 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962Water
Solvent
HCID 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 5 1/2 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 5 1/2 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-c81a931288d54cf7a1181f742388648a
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04092330

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes