HCID 14648650, compound → HCID 67931152, compound

HRID 345159Notes

Reaction equation

HRID 345159 reaction equation
[NH2:1][C:2]1(C(OC)=O)[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19].O.O.O.[I-].[Li+]>N1C=CC=CC=1>[NH2:1][C@H:2]1[C@@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19].[NH2:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19]

Participants

5

Reactant 2

HCID 14648650HCID 14648650, compoundHCID 23688288Lithium iodide--water (1/1/3)

Product 2

HCID 67931152HCID 67931152, compoundHCID 67931257HCID 67931257, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 17.98 g of 3-amino-3-methoxycarbonyl-4-phenyl-1,3,4,5-tetrahydro-1-benzazepin-2(2H)-one, 21.76 g of lithium iodide trihydrate and 400 ml of dried pyridine is stirred under reflux for 2 days. To the residue obtained after the mixture is concentrated under reduced pressure, an aqueous solution of potassium carbonate, an aqueous solution of sodium thiosulfate and chloroform are added, and the organic substance is extracted. The chloroform layer is dried and concentrated. The obtained residue is subjected to silica gel chromatography (eluent: chloroform:methanol =20:1) to give 5.6 g of cis-3-amino-4-phenyl-1,3,4,5-tetrahydro-1-benzazepin-2(2H)-one and 5.44 g of trans-3-amino-4-phenyl-1,3,4,5-tetrahydro-benzazepin-2(2H)-one.

Workup

  1. temperatureunder reflux for 2 days
  2. customTo the residue obtained after the mixture
  3. concentrationis concentrated under reduced pressure
  4. additionan aqueous solution of potassium carbonate, an aqueous solution of sodium thiosulfate and chloroform are added
  5. extractionthe organic substance is extracted
  6. dry with materialThe chloroform layer is dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-868afd92098b4c77aafa551253130fa8
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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