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

HRID 1473003Notes

Reaction equation

HRID 1473003 reaction equation
CS(O[CH2:6][CH2:7][CH:8]([C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)=O.[CH:30]([NH:33][CH:34]([CH3:36])[CH3:35])([CH3:32])[CH3:31]>O>[CH:30]([N:33]([CH2:6][CH2:7][C@@H:8]([C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:34]([CH3:36])[CH3:35])([CH3:32])[CH3:31].[CH:30]([N:33]([CH2:6][CH2:7][CH:8]([C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:34]([CH3:36])[CH3:35])([CH3:32])[CH3:31]

Participants

5

Reactant 2

HCID 7912DiisopropylamineHCID 56849004HCID 56849004, compound2×

Product 2

HCID 129724153-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amineHCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 g 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropyl methanesulfonate of formula (D) and 400 ml diisopropyl amine and 100 ml water under closed reaction condition in SSR autoclave for 48 to 50 hours. The reaction mass was cooled to 0° C. to 5° C. followed by filtration and then washing with 25 ml water. After distillation of solvent completely under vacuum and work up with MDC and water in acidic pH and basic afforded title compound N,N-Diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine of formula (E) in residue form.

Workup

  1. customreaction condition in SSR autoclave for 48 to 50 hours
  2. temperatureThe reaction mass was cooled to 0° C. to 5° C.
  3. filtrationfollowed by filtration
  4. washwashing with 25 ml water
  5. distillationAfter distillation of solvent completely under vacuum

Sources & evidence

ORD record
ord-1297e710f272457ba0db711cb760599a
Source dataset
uspto-grants-2015_04
Patent number
US09012678B2

Reaction notes

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