Hydrazine → Tert-butyl 4-(3-(5-aminopent-1-ynyl)phenoxy)piperidine-1-carboxylate

HRID 473514Notes

Reaction equation

HRID 473514 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:17]1[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=1)[O:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.NN>C(O)C>[NH2:3][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:17]1[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=1)[O:20][CH:21]1[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67202792Tert-butyl 4-(3-(5-(1,3-dioxoisoindolin-2-yl)pent-1-ynyl)phenoxy)piperidine-1-carboxylate

Product 1

HCID 67203672Tert-butyl 4-(3-(5-aminopent-1-ynyl)phenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-(1,3-dioxoisoindolin-2-yl)pent-1-ynyl)phenoxy)piperidine-1-carboxylate (10.65 g, 21.8 mmol) in ethanol (100 ml) was added hydrazine (2.1 g, 65.4 mmol). The resulting solution was heated under reflux for two hours, then cooled to room temperature, filtered and concentrated. The residue was dissolved in ethyl acetate (200 ml). The resulting solution was extracted with water twice, brine once, then dried over magnesium sulfate. The resulting solution was filtered and concentrated to yield tert-butyl 4-(3-(5-aminopent-1-ynyl)phenoxy)piperidine-1-carboxylate as a brown oil. MH+ 359.33

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for two hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate (200 ml)
  6. extractionThe resulting solution was extracted with water twice
  7. dry with materialbrine once, then dried over magnesium sulfate
  8. filtrationThe resulting solution was filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-28b58956e10947dbbcbada693d609cdd
Source dataset
uspto-grants-2014_01
Patent number
US08633322B2

Reaction notes

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