Hydrochloric Acid → (2S)-Piperidine-2-carboxamide hydrochloride

HRID 1155091Notes

Reaction equation

HRID 1155091 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:9][CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH2:5])=[O:4].[ClH:17]>C(OCC)(=O)C.CCOCC>[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH2:5])=[O:4].[ClH:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2756821(s)-1-n-boc-pipecolamide

Product 1

HCID 22818427(2S)-Piperidine-2-carboxamide hydrochlorideYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1.6 g (7 mmoles) of BOC-HPro-NH2 are dissolved in 10 ml of ethyl acetate under heating. The solution is cooled to room temperature, and 10 ml of a 6 n hydrochloric acid solution in ethyl acetate are added. After one hour of standing the mixture is diluted with ether, the separated precipitate is triturated and then filtered off. 1.05 g (91%) of H-HPro-NH2.HCl are obtained; m.p.: 178°-180° C., Rf6 =0.32, [α]D25 =+26.2° (c=1%, in methanol).

Workup

  1. temperatureunder heating
  2. customthe separated precipitate is triturated
  3. filtrationfiltered off

Sources & evidence

ORD record
ord-49bd469b5fd848d08327f4a6591563db
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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