1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 23138897, compound

HRID 1171732Notes

Reaction equation

HRID 1171732 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11](/[CH:12]=[C:13]2\[CH2:14][N:15]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:17][CH:18]\2O)=[CH:10][N:9]=[CH:8]1)=[O:5])[CH3:2].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[C:55]([OH:58])(=[S:57])[CH3:56]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:55]([S:57][CH:18]1[CH2:17][CH2:16][N:15]([C:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:14]/[C:13]/1=[CH:12]\[C:11]1[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:8]=[N:9][CH:10]=1)(=[O:58])[CH3:56]

Participants

6

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138491HCID 23138491, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23138897HCID 23138897, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (3.15 g) in toluene (50 ml) were added N,N-dimethylformamide dineopentyl acetal (3.5 ml) and thioacetic acid (0.89 ml) at room temperature. After being stirred at room temperature for 1 hour, the mixture was diluted with ethyl acetate, washed successively with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure followed by purification of the residue by silica gel chromatography using ethyl acetate and hexane (1:4 to 1:0) as eluents gave crude (E)-4-(acetylsulfanyl)-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (3.29 g) as a yellow amorphous solid.

Workup

  1. washwashed successively with water
  2. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  3. customRemoval of the solvent under reduced pressure
  4. customfollowed by purification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-2238cb27067b43198d9b552a34d77666
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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