Hydrochloric Acid → HCID 66601607, compound

HRID 604318Notes

Reaction equation

HRID 604318 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4][CH2:3]1.CO.[ClH:29]>C1(C)C=CC=CC=1>[ClH:29].[ClH:29].[N:14]1([C:13]2[C:8]([N:5]3[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59438212HCID 59438212, compound

Product 1

HCID 66601607HCID 66601607, compoundYield 99.47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

Add t-Butyl 4-(2-(4-hydroxypiperidin-1-yl)pyridin-3-yl)piperazine-1-carboxylate (306.5 g, 0.846 mol) to a 12-liter flask, followed by methanol (613 ml) and toluene (3.06 L). Stir the mixture to give a solution and then add the methanolic HCl solution (579 mL). Heat the solution to 35° C. for 2 hr. followed by 4 hr. at ambient temperature. Filter off the resulting crystalline product, wash the crystals with toluene, and then dry in a vacuum oven at 40-45° C. to provide 1-(3-(piperazin-1-yl)pyridin-2-yl)piperidin-4-ol dihydrochloride as a crystalline solid (283.5 g, 99.47%). 1H NMR 300 MHz (DMSO) δ 9.624 (bs, 2H) 7.890 (dd, J=6.4 Hz, 1H), 7.633 (d, J=7.75 Hz, 1H), 7.137 (m, 1H), 3.916 (bm, 2H), 3.727 (bm, 1H), 3.236 (bs, 9H), 1.877 (bm, 2H), 1.515 (bm, 2H).

Workup

  1. customto give a solution
  2. customat ambient temperature
  3. filtrationFilter off the resulting crystalline product
  4. washwash the crystals with toluene
  5. customdry in a vacuum oven at 40-45° C.

Sources & evidence

ORD record
ord-cb44b3e3df7148b7b89bae4b1dd3f8dd
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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