Ammonia → HCID 68127028, compound

HRID 1580467Notes

Reaction equation

HRID 1580467 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]=3[N:15](N)[C:14]=2[CH:13]=[CH:12][C:11]=1CC1C=CC=CC=1)C1C=CC=CC=1.[ClH:33].[NH:34]1[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]1.S(=O)(=O)(O)O.N>O.C(O)C>[ClH:33].[CH2:24]1[C:16]2[N:15]3[C:37]4[CH:38]=[CH:39][N:34]=[CH:35][C:36]=4[C:13]4[CH2:12][CH2:11][CH:10]=[C:20]([C:14]=43)[CH:19]=[CH:18][C:17]=2[CH2:21][CH2:22][CH2:23]1

Participants

7

Reactant 4

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

Product 1

HCID 68127028HCID 68127028, 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 and cooled; a solution of 20 g. of concentrated sulfuric acid in 250 ml. ethanol was added. The resulting mixture was reheated on the steam bath for additional 40 minutes; the solution which formed was cooled, basified with ammonia, and diluted with 1.1 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 etheral 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 1N hydrochloric acid, and dried in vacuo at 100° to yield 1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][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.

Workup

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

Sources & evidence

ORD record
ord-2364c7f5442c42579c18bd7e6181643f
Source dataset
uspto-grants-1976_01
Patent number
US03932650

Reaction notes

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