HCID 20319968, compound → HCID 20319969, compound

HRID 866630Notes

Reaction equation

HRID 866630 reaction equation
C(O)(=O)/C=C/C(O)=O.[NH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][CH:11]([CH2:20][NH2:21])[CH2:10]1>O>[NH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][CH:11]([CH2:20][NH2:21])[CH2:10]1

Participants

3

Reactant 1

HCID 20319968HCID 20319968, compound

Product 1

HCID 20319969HCID 20319969, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.8 g of the fumarate salt of Example 1 were dissolved in 100 ml of refluxing water and the mixture was filtered and cooled. The filtrate was made alkaline with a concentrated ammonium solution and was extracted with methylene chloride. The organic extracts were washed with water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure to obtain 2.9 g of 2,3,4,5-tetrahydro-[1H]-1-benzazepine-3-methanamine in the form of a yellow oil which was cooled on an ice bath. 0.62 ml of formic acid were added thereto and the mixture was stirred and heated for 15 minutes on a bath at 150° C. The mixture was cooled to about 20° C and was dissolved in 30 ml of methylene chloride. The mixture was dried and filtered and the filtrate was evaporated to dryness to obtain 3.3 g of a brown oil which was chromatographed over silica gel. Elution with a 9-1 chloroform-methanol mixture yielded two fractions, the first being 700 mg of N-[(1-formyl-2,3,4,5-tetrahydro-[1H]-1-benzazepine-3-yl)-methyl -formamide as a colorless oil with an Rf = 0.45. The latter was crystallized from 0.5 ml of ethyl acetate and was vacuum filtered to obtain 410 mg of the said product in the form of colorless crystals melting at 130° C. The second fraction was 1.3 g of N-[(2,3,4,5-tetrahydro-[1H]-1-benzazepine-3-yl)-methyl] -formamide in the form of a colorless oil with an Rf = 0.4. The latter was crystallized from 2 ml of ether and was vaccum filtered to obtain 1.25 g of the said product in the form of colorless crystals melting at 120° and then 160° C.

Workup

  1. filtrationthe mixture was filtered
  2. temperaturecooled
  3. extractionwas extracted with methylene chloride
  4. washThe organic extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b2e04192d9c941bb87604c28b63066e2
Source dataset
uspto-grants-1978_07
Patent number
US04100278

Reaction notes

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