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Diethyl Ether → 2-[1-[2-(Tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethylamine

HRID 2223871
Notes
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Reaction equation

HRID 2223871 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][N:29]2C(=O)C3=CC=CC=C3C2=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.NN.C(OCC)C>C(O)C>[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][NH2:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[Si:2]([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 59714868N-[2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]-phthalimide

Product 1

HCID 597149732-[1-[2-(Tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethylamineYield 104%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[2-[1-[2(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]-ethyl]phthalimide (1.52 g) dissolved in ethanol (30 mL) was added hydrazine monohydrate. The reaction solution was heated under reflux for 4 hours. To this was added diethyl ether and the insolbles were filtered off. The solvent was then distilled off under reduced pressure. To this was added chloroform, and the solution was made basic by addition of a 1N aqueous hydroxide solution. The solution was then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then, the solvent was distilled off under reduced pressure to give the title compound (1.20 g).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 4 hours
  3. filtrationthe insolbles were filtered off
  4. distillationThe solvent was then distilled off under reduced pressure
  5. additionTo this was added chloroform
  6. additionthe solution was made basic by addition of a 1N aqueous hydroxide solution
  7. extractionThe solution was then extracted with chloroform
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e31492b101284082967088fa9d8667a3
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07375115B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes