Water → Dibenzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]amine

HRID 1817746Notes

Reaction equation

HRID 1817746 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][OH:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]C([O-])(C)C.[K+].I[CH2:31][C:32]1[N:33]=[C:34]([C:38]2[CH:43]=[CH:42][C:41](C)=[CH:40][CH:39]=2)[O:35][C:36]=1[CH3:37].O>C1(Cl)C=CC=CC=1.CC(OC)(C)C>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][O:16][CH2:31][C:32]2[N:33]=[C:34]([C:38]3[CH:39]=[C:40]([CH3:24])[CH:41]=[CH:42][CH:43]=3)[O:35][C:36]=2[CH3:37])[CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 219803112-(4-Methylphenyl)-4-iodomethyl-5-methyloxazoleHCID 23665647Potassium tert-butoxide2×HCID 596592093-Dibenzylaminocyclohexylmethanol

Product 1

HCID 57882729Dibenzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]amineYield 92.3%

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

5.0 g of 3-dibenzylaminocyclohexylmethanol and 1.72 g of KOtBu were initially charged in PhCl, and 7.59 g of 4-iodomethyl-5-methyl-2-p-tolyloxazole were added a little at a time. At room temperature and under an atmosphere of argon, the mixture was stirred for 2 days. Another 1.0 g of KOtBu was added, and stirring of the mixture was continued. The reaction was then complete. For work-up, water and MTBE were added, the phases were separated and the organic phase was washed with water and sat. NaCl solution, dried over MgSO4 and concentrated. Chromatography of the residue on silica gel (heptane/ethyl acetate 10:1→3:1) gave 7.0 g of dibenzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]amine as a brown oil.

Workup

  1. stirringstirring of the mixture
  2. customthe phases were separated
  3. washthe organic phase was washed with water and sat. NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b01133df9a53482ba7441c48ed13fe2e
Source dataset
uspto-grants-2009_10
Patent number
US07598281B2

Reaction notes

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