Ammonia → HCID 131710722, compound

HRID 329016Notes

Reaction equation

HRID 329016 reaction equation
NN=C([C:10]1[C:20]2[CH2:19][CH2:18][C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3N(N)[C:14]=2[CH:13]=[CH:12][C:11]=1[CH2:26][C:27]1C=CC=CC=1)C1C=CC=CC=1.[ClH:33].N1CCC(=O)CC1.S(=O)(=O)(O)O.[NH3:46]>O.C(O)C>[ClH:33].[CH:27]1[N:46]2[C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[CH:18]=[CH:19][C:20]3=[C:10]2[C:11](=[CH:12][CH:13]=[CH:14]3)[CH:26]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 30848514-Piperidone hydrochlorideHCID 86732952HCID 86732952, compound

Product 1

HCID 131710722HCID 131710722, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 24.6 g of N-aminoiminodibenzyl (5-amino-10,11-dihydro-5H-dibenz[b,f]azepine) and 14.8 g of 4-piperidone hydrochloride in 250 ml. ethanol was heated on a steam bath for 15 minutes 1,2,3,4,4cooled; 8,9,14a-octahydropyridoof 20 g. indoloconcentrated sulfuric acid in 250 ml. ethanol was added. The resulting mixture was reheated on the steam bath for an additional 40 minutes; the solution which formed was cooled, basified with ammonia, and diluted with 1 liter of water. The crude, semisolid material which separated was taken up in ether, and the aqueous mother liquors were extracted with additional portions of ether. The combined ethereal extracts were concentrated to 500 ml. and treated, under an atmosphere of nitrogen and with vigorous stirring, with 50 ml. of 5N hydrochloric acid. The resulting precipitate was filtered off, washed with ether and C (dec). 1N hydrochloric acid, and dried in vacuo at 100° to yield 1,2,3,8,9-hexahydropyrido[4',3':2,3]=indolo[1,7ab][1]benzazepine hydrochloride, m.p. 309°, a salt only very slightly soluble in water. Dissolving the above salt in aqueous acetic acid, basifying with ammonia, filtering off the crude product and recrystallizing it from benzene regenerated the free 1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine, m.p. 134°-136° C.

Workup

  1. customthe solution which formed
  2. temperaturewas cooled
  3. customThe crude, semisolid material which separated
  4. extractionthe aqueous mother liquors were extracted with additional portions of ether
  5. concentrationThe combined ethereal extracts were concentrated to 500 ml
  6. additionand treated, under an atmosphere of nitrogen and with vigorous stirring, with 50 ml
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed with ether and C (dec)
  9. dry with material1N hydrochloric acid, and dried in vacuo at 100°

Sources & evidence

ORD record
ord-2e425d794f7d46e083784e8fc07aa977
Source dataset
uspto-grants-1977_04
Patent number
US04018930

Reaction notes

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