Hydrochloric Acid → 4-Benzyl-4-(4-methoxybenzylamino)cyclohexanone

HRID 2422396Notes

Reaction equation

HRID 2422396 reaction equation
Cl.[CH2:2]([C:9]1([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([C:9]1([NH:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67127336(8-Benzyl-1,4-dioxaspiro[4,5]dec-8-yl)(4-methoxybenzyl)amine

Product 1

HCID 671272124-Benzyl-4-(4-methoxybenzylamino)cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6 M hydrochloric acid (7 ml) was added to a solution of (8-benzyl-1,4-dioxaspiro[4,5]dec-8-yl)(4-methoxybenzyl)amine (1.2 g, 3.3 mmol) in acetone (17 ml). The reaction solution was stirred for 20 h at room temperature, then made alkaline (pH˜9) with 25% potassium carbonate solution and extracted with diethyl ether (3×20 ml). The combined organic phases were dried with sodium sulfate and concentrated to approx. 10 ml under vacuum. The precipitated deposit was filtered off and dried under vacuum. Yield: 790 mg (74%), white solid. Melting point: 122-124° C.

Workup

  1. extractionextracted with diethyl ether (3×20 ml)
  2. dry with materialThe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated to approx. 10 ml under vacuum
  4. filtrationThe precipitated deposit was filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7e69568f85d84bd29956f7c1f43a76f8
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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