Hydrazine hydrate (1:1) → Tert-butyl(cis)-4-(2-aminoethyl)-3,5-dimethyl-1-piperazinecarboxylate

HRID 2119386Notes

Reaction equation

O.NN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[CH2:15][CH2:16][N:17]1[C@@H:22]([CH3:23])[CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][C@H:18]1[CH3:31]>CO>[NH2:6][CH2:15][CH2:16][N:17]1[C@@H:22]([CH3:23])[CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:19][C@H:18]1[CH3:31]

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrazine hydrate (0.11 ml) was added to a solution of tert-butyl (cis)-4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3,5-dimethyl-1-piperazinecarboxylate (0.736 g) [see Preparation 6] in methanol (1.1 ml). The reaction mixture was then stirred at 50° C. for 18 hours, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and 10% citric acid. The aqueous layer was separated, basified with potassium carbonate, and the product extracted with tetrahydrofuran:ethyl acetate, 1:1, several times. The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure to afford tert-butyl (cis)-4-(2-aminoethyl)-3,5-dimethyl-1-piperazinecarboxylate (0.33 g) as a oil.

Workup

customafter which time the solvent was removed under reduced pressure
customthe residue partitioned between ethyl acetate and 10% citric acid
customThe aqueous layer was separated
extractionthe product extracted with tetrahydrofuran
dry with materialThe combined organic layers were dried over magnesium sulphate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-309fb68b2d35401a9a5ba2ecf4f6d2f2
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686357B1

Reaction notes

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