Dichloromethane → (3R)-N,N-dimethylpiperidin-3-amine,hydrochloride

HRID 1366487Notes

Reaction equation

HRID 1366487 reaction equation
[CH3:1][N:2]([CH3:16])[C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.C(Cl)[Cl:18]>Cl.O1CCOCC1>[ClH:18].[ClH:18].[CH3:1][N:2]([CH3:16])[C@@H:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 44630594tert-Butyl (3R)-3-(dimethylamino)piperidine-1-carboxylate

Product 1

HCID 117601420(3R)-N,N-dimethylpiperidin-3-amine,hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Dimethylethyl (3R)-3-(dimethylamino)-1-piperidinecarboxylate (5.0 g crude, 21.12 assumed mmol) was dissolved and stirred in a mixture of CH2Cl2 (10 mL) and 4M HCl in dioxane (21 mL, 4 eqv.) A white precipitate formed. The reaction appeared to stall at approximately 70% completion, and therefore another 21 mL of 4M HCl in dioxane was added to the reaction mixture. After 4 h at room temperature, the solvent was evaporated, providing (3R)—N,N-dimethyl-3-piperidinamine, dihydrochloride as a white solid (3.5 g, 89% for two steps).

Workup

  1. customformed
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1ce33da1a35043e693f5b046efef7be8
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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