Hydrochloric Acid → (S)-Piperazine-2-carboxylic acid dihydrochloride

HRID 1586536Notes

Reaction equation

HRID 1586536 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C@H:2]1[C:7]([O:9]C(C)(C)C)=[O:8].[ClH:14]>O>[ClH:14].[ClH:14].[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45115680HCID 45115680, compound

Product 1

HCID 2734260(S)-Piperazine-2-carboxylic acid dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The crude tert-butyl (S)-piperazine-2-carboxylate from Example 7 was stirred in 2.9 g of water and 2.1 g (18.4 mmol) of 32 percent hydrochloric acid for 20 minutes at 100° C. The mixture was cooled to 0° C. and stirred for a further 1 hour. The hydrochloride which had precipitated out was filtered off and washed with 10 ml of dichloromethane. The yield of the title compound was 0.24 g (41 percent, based on tert-butyl pyrazinecarboxylate). The ee value was 77.6 percent.

Workup

  1. customThe hydrochloride which had precipitated out
  2. filtrationwas filtered off
  3. washwashed with 10 ml of dichloromethane

Sources & evidence

ORD record
ord-0ee039259ffc44829d7a2b491a05c2bb
Source dataset
uspto-grants-1999_08
Patent number
US05945534

Reaction notes

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