Diisopropylamine → 3-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

HRID 227197Notes

Reaction equation

HRID 227197 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[C:16]1C(CCCC2C=CC=CC=2)=C(C)C=[CH:20][C:21]=1S([O-])(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36]([NH:39][CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]>C(#N)C>[CH:36]([N:39]([CH2:20][CH2:21][CH:16]([C:10]1[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 86749863HCID 86749863, compound

Product 1

HCID 129724153-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amineYield 163.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl-p-toluenesulfonate (115 g, 0.2 mole) was dissolved in a mixture of acetonitrile (150 g) and diisopropylamine (202 g, 2.0 mole) and the mixture was refluxed for 4 days. The solution was evaporated, and to the resulting syrup was added sodium hydroxide (2M, 200 mL). The mixture was concentrated, cooled and then extracted with diethyl ether. The ethereal layer was extensively washed with water. The amine was extracted with excess sulfuric acid (1M). The aqueous layer was washed with diethyl ether and then basified with sodium hydroxide (11M). The mixture was then extracted with diethyl ether. The organic layer was washed with water, dried over sodium sulfate, filtered and then evaporated to give 78.6 g (78%) of N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine as a pale yellow oil. The 1-H N.M.R spectrum was in accordance with the above structure.

Workup

  1. temperaturethe mixture was refluxed for 4 days
  2. customThe solution was evaporated
  3. additionto the resulting syrup was added sodium hydroxide (2M, 200 mL)
  4. concentrationThe mixture was concentrated
  5. temperaturecooled
  6. extractionextracted with diethyl ether
  7. washThe ethereal layer was extensively washed with water
  8. extractionThe amine was extracted with excess sulfuric acid (1M)
  9. washThe aqueous layer was washed with diethyl ether
  10. extractionThe mixture was then extracted with diethyl ether
  11. washThe organic layer was washed with water
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. customevaporated

Sources & evidence

ORD record
ord-23f2757f39c34fb8886c81d129f45b24
Source dataset
uspto-grants-2009_07
Patent number
USRE040851E1

Reaction notes

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