Ammonia → HCID 67923525, compound

HRID 973959Notes

Reaction equation

HRID 973959 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH2:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.P(=O)(O)(O)O.[CH2:18]([N:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>C(O)(=O)C.CO.CCOCC.C(OCC)(=O)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[C:19]1([CH2:18][N:25]2[CH2:26][CH:27]=[C:28]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[C:6]([C:10]([NH2:12])=[O:11])[CH:5]=4)[NH:1][CH:2]=3)[CH2:29][CH2:30]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 1004Phosphoric AcidHCID 192201-Benzyl-4-piperidoneHCID 444266Maleic AcidHCID 149732201H-Indole-5-carboxamide

Product 1

HCID 67923525HCID 67923525, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

A suspension of 1H-indole-5-carboxamide (0.4 g) in galcial acetic acid (20 ml) was heated to 80°under nitrogen, and the resulting solution was treated with aqueous phosphoric acid (2N; 7 ml). Freshly distilled 1-benzyl-4-piperidone (1.4 g) in glacial acetic acid (5 ml) was added and the reaction mixture was stirred at 70° for 18 h, cooled, and poured into a mixture of ice and 0.88 ammonia solution (50 ml) with ice bath cooling. Ethyl acetate (50 ml) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (4×60 ml), and the combined organic extracts were dried (MgSO4) and evaporated to dryness. The resulting oil was chromatographed on Merck Kieselgel 60 (100 g) eluting with 10% methanol in ethyl acetate. Evaporation of the solvent gave a foam which was treated with maleic acid in methanol/ether to give the title compound as microcrystals (0.19 g), m.p. 164°-166°.

Workup

  1. temperaturewas heated to 80°under nitrogen
  2. temperaturecooled
  3. temperaturecooling
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (4×60 ml)
  6. dry with materialthe combined organic extracts were dried (MgSO4)
  7. customevaporated to dryness
  8. customThe resulting oil was chromatographed on Merck Kieselgel 60 (100 g)
  9. washeluting with 10% methanol in ethyl acetate
  10. customEvaporation of the solvent
  11. customgave a foam which

Sources & evidence

ORD record
ord-aaf204fdf1a34f24971a12201ed7ec08
Source dataset
uspto-grants-1991_11
Patent number
US05066660

Reaction notes

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