Hydrochloric Acid → HCID 12286596, compound

HRID 1580128Notes

Reaction equation

HRID 1580128 reaction equation
C(C1CCCCC1)(=O)N.Cl.S(=O)(=O)(O)O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:24]2([C:31](=[O:33])[NH2:32])[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1.BrBr.Br.[NH+]1C=CC=CC=1.BrC1CC(C2C=CC=C(OC)C=2)(C(=O)N)CCC1=O>C(COC)OC.C(O)C.CO.O1CCCC1.C(O)(=O)C>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:24]23[CH2:25][CH:26]([NH:32][C:31]2=[O:33])[C:27](=[O:30])[CH2:28][CH2:29]3)[CH:21]=[CH:22][CH:23]=1

Participants

13

Reactant 7

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14283CyclohexanecarboxamideHCID 24408BromineHCID 12286593HCID 12286593, compoundHCID 21226041Pyridinium hydrobromideHCID 21564944HCID 21564944, compound

Product 1

HCID 12286596HCID 12286596, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

First of all, 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]-octane-7-one (VIII) is prepared by the six steps of (I) hydrolyzing 4-(3-methoxyphenyl)-4-cyano-1,1,-ethylenedioxy-cyclohexane (VII) with an alkali metal hydroxide(e.g., sodium hydroxide, potassium hydroxide) under heating in a solvent (e.g., methanol, ethanol, ethyleneglycol, a mixture of one of these solvents and water) to give 4-(3-methoxyphenyl)-4-carbamoyl-1,1-ethylenedioxy-cyclohexane, (2) reacting said carbamoyl-cyclohexane with an acid(e.g., hydrochloric acid, sulfuric acid, acetic acid) under heating, (3) brominating the resultant 4-(3-methoxyphenyl)-4-carbamoyl-cyclohexanone with bromine or pyridinium hydrobromide perbromide (C5H5N+HBr-) at room temperature in a solvent (e.g., acetic acid, tetrahydrofuran), (4) reacting the resultant 2-bromo-4-(3-methoxyphenyl)-4-carbamoyl-cyclohexanone with an alkali metal hydride (e.g., sodium hydride) or an alkali metal alkoxide (e.g., sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide) at room temperature in a solvent(e.g., methanol, ethanol, dimethoxyethane) to give 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione, (5) refluxing a mixture of said product and hydrazine hydrate under heating in a solvent (e.g., ethanol, ethyleneglycol), and then (6) heating the resultant 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione-4-hydrazone in the presence of an alkali agent(e.g., potassium hydroxide, potassium tert.-butoxide) in a solvent (e.g., toluene).

Workup

  1. customat room temperature
  2. customat room temperature

Sources & evidence

ORD record
ord-d213f94bfbaa4b38b83e37cc7d1226cb
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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