HCID 20304620, compound → HCID 20304637, compound

HRID 1732696Notes

Reaction equation

HRID 1732696 reaction equation
[ClH:1].NN1C2C=CC=CC=2COCC1.[CH2:14]1[CH2:20][O:19][CH2:18][C:17]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:25]4[CH2:30][NH:29][CH2:28][CH2:27][C:26]=4[N:15]1[C:16]=23>>[ClH:1].[CH2:14]1[CH2:20][O:19][CH2:18][C:17]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:25]4[CH2:30][NH:29][CH2:28][CH2:27][C:26]=4[N:15]1[C:16]=23

Participants

3

Reactant 2

HCID 20304620HCID 20304620, compoundHCID 20304799HCID 20304799, compound

Product 1

HCID 20304637HCID 20304637, compound

Procedure

1,2,3,5-Tetrahydro-4,1-benzoxazepine, prepared according to E. Testa and L. Fontanella, Fr. Pat. No. 1,405,271, is converted to the corresponding 5-nitroso derivative as described in Example 1 obtained as yellow crystals, m.p. 62°-64° C. The latter, 8.3 g, is dissolved in 130 ml of methanol. To the resulting solution, cooled to 10°-15° C. there is added 20 g of Zn dust in small portions along with 25 ml of acetic acid, added dropwise. After the addition is complete, the mixture is stirred at room temperature for 3 hours and then filtered. The filtrate is stripped of the solvent under reduced pressure and the oily residue is treated with 5 N HCl to yield 1-amino-1,2,3,5-tetrahydro-4,1-benzoxazepine hydrochloride, which is filtered and washed on the filter with ether, m.p. 229°-230°. The aforementioned hydrazine hydrochloride (3 g.) is reacted with 2.6 g of 4-piperidone hydrochloride in 30 ml of ethanol saturated with gaseous HCl by heating to reflux for 2 hours. The HCl salt of 1,2,8,9,10,11-hexahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-jk][4,1]benzoxazepine separates out in the course of the reaction. The product was cooled, filtered, and recrystallized from ethanol. Melting point of the resulting product was 296°-297°.

Workup

  1. filtrationis filtered
  2. washwashed on the
  3. filtrationfilter with ether, m.p. 229°-230°
  4. customThe aforementioned hydrazine hydrochloride (3 g.) is reacted with 2.6 g of 4-piperidone hydrochloride in 30 ml of ethanol saturated with gaseous HCl
  5. temperatureby heating
  6. temperatureto reflux for 2 hours
  7. temperatureThe product was cooled
  8. filtrationfiltered
  9. customrecrystallized from ethanol
  10. customwas 296°-297°

Sources & evidence

ORD record
ord-3bb0769d1500418caef68d70623e7d2e
Source dataset
uspto-grants-1980_12
Patent number
US04238607

Reaction notes

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