Hydrochloric Acid → 1-[(3R)-pyrrolidin-3-yl]piperidine dihydrochloride

HRID 1691978Notes

Reaction equation

HRID 1691978 reaction equation
[N:1]1([C@@H:7]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:19].O1CCOCC1>CO>[ClH:19].[ClH:19].[NH:9]1[CH2:10][CH2:11][C@@H:7]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66905725(R)-tert-butyl 3-(piperidin-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 669057171-[(3R)-pyrrolidin-3-yl]piperidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred, room temperature solution of (R)-tert-butyl 3-(piperidin-1-yl)pyrrolidine-1-carboxylate (Reference Example 5b, 6.87 g, 27.0 mmol) in methanol (100 mL) was treated with 4 N HCl in dioxane (67.5 mL, 0.2700 mole). The reaction mixture was stirred at room temperature overnight, then volatiles were removed under reduced pressure. The resulting solid was crystallized from methanol/ether to provide (R)-1-(pyrrolidin-3-yl)piperidine dihydrochloride. 1H NMR (300 MHz, CD3OD) δ ppm 1.46-2.03 (m, 6H), 2.32-2.46 (m, 1H), 2.53-2.63 (m, 1H), 2.95-3.20 (m, 2H), 3.33-3.43 (m, 1H), 3.47-3.72 (m, 4H), 3.78-3.85 (m, 1H), 4.09 (pentet, J=8 Hz, 1H); MS (ESI) m/z 155 (M+H)+.

Workup

  1. customvolatiles were removed under reduced pressure
  2. customThe resulting solid was crystallized from methanol/ether

Sources & evidence

ORD record
ord-c18670a378974248a2de08c400d4139c
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

Loading…