HCID 53742785, compound → Tert-butyl(cis)-4-(2-aminoethyl)-3,5-dimethyl-1-piperazinecarboxylate

HRID 1276162Notes

Reaction equation

HRID 1276162 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][N:14]1[C@@H:19]([CH3:20])[CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][C@H:15]1[CH3:28]>CO>[NH2:3][CH2:12][CH2:13][N:14]1[C@@H:19]([CH3:20])[CH2:18][N:17]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:16][C@H:15]1[CH3:28]

Participants

3

Reactant 1

HCID 53742785HCID 53742785, compound

Product 1

HCID 53985942Tert-butyl(cis)-4-(2-aminoethyl)-3,5-dimethyl-1-piperazinecarboxylateYield 67.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

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, bastified 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

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

Sources & evidence

ORD record
ord-3c3eb8255d7a41ea8b8d9644fa7f3644
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

Loading…