Sodium Hydroxide → HCID 44512845, compound

HRID 1011628Notes

Reaction equation

HRID 1011628 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[CH3:11][N:12]([CH3:26])[C:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.FC(F)(F)S(O)(=O)=O.[OH-:35].[Na+]>ClCCl>[CH3:11][N:12]([CH3:26])[C:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17][C:16]([C:1]2[O:35][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[CH3:3])([C:3]2[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[CH3:1])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 889393-MethylbenzofuranHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 44512845HCID 44512845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-methylbenzofuran (354 mg, 3 mmol) together with 4-(dimethylamino)-4-phenylcyclohexanone (651 mg, 3 mmol, synthesis cf. WO2008009415, ketone unit Ket-10) was dissolved in dichloromethane (25 ml) and mixed with trifluoromethane sulphonic acid (0.3 ml, 3.4 mmol). The batch was stirred for 20 h at RT. For work up the reaction mixture was mixed with 2N NaOH (10 ml). The mixture was stirred a further 20 min. After separation of the phases the aqueous phase was extracted with dichloromethane (3×20 ml). The combined organic extracts were dried over MgSO4 and then concentrated to low volume. The raw product (950 mg) obtained was purified by column chromatography (mobile solvent: EtOAc) and then recrystallised from ethanol (60 ml).

Workup

  1. stirringThe mixture was stirred a further 20 min
  2. customAfter separation of the phases the aqueous phase
  3. extractionwas extracted with dichloromethane (3×20 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-76926db5153642309a734ceefd1b7e67
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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