tert-Butoxy bis(dimethylamino)methane → 6-[1-Dimethylamino-methylidene]-2-methyl-2-phenylcyclohexanone

HRID 2076042Notes

Reaction equation

HRID 2076042 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].C(O[CH:20](N(C)C)[N:21]([CH3:23])[CH3:22])(C)(C)C>>[CH3:20][N:21]([CH3:23])[CH:22]=[C:4]1[C:3](=[O:8])[C:2]([CH3:1])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:7][CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 3499432-Methyl-2-phenylcyclohexanone

Product 1

HCID 670961136-[1-Dimethylamino-methylidene]-2-methyl-2-phenylcyclohexanoneYield 101.9%

Procedure

A mixture 2-methyl-2-phenylcyclohexanone (94 mg, 0.5 mmol) and tert.-butoxy-bis-(dimethylamino)-methane (0.16 mL, 0.77 mmol) was stirred at 110° C. for 1.5 h, whereupon it was cooled and evaporated under reduced pressure. Toluene (3 mL) was added to the residue and the solution was evaporated again to give the title compound (124 mg) as red oil which was used without further purification. MS ISP (m/e): 244.4 [(M+H)+].

Workup

  1. temperaturewas cooled
  2. customevaporated under reduced pressure
  3. additionToluene (3 mL) was added to the residue
  4. customthe solution was evaporated again

Sources & evidence

ORD record
ord-9b799946d1694e1c83eaed6749e7fbbf
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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