Hydrochloric Acid → 1,4′-Bipiperidine, 4-methyl-, hydrochloride (1:2)

HRID 419355Notes

Reaction equation

HRID 419355 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[ClH:21]>>[ClH:21].[ClH:21].[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57678157HCID 57678157, compound

Product 1

HCID 568315941,4′-Bipiperidine, 4-methyl-, hydrochloride (1:2)Yield 36.3%

Procedure

1,1-Dimethylethyl 4-methyl-1,4′-bipiperidine-1′-carboxylate (33.0 g, 117 mmol) in HCl (60.0 mL, 4M in MeOH, 240 mmol) was refluxed at 60° C. for 1 h. The reaction was concentrated and the residue was taken up in MeOH (100 mL), filtered and concentrated to provide the title compound of step B (10.8 g, 42.5 mmol, 36%). 1H NMR (300 MHz, D2O) δ ppm 0.85 (d, J=6.22 Hz, 3H), 1.22-1.41 (m, 2H), 1.51-1.70 (m, 1H), 1.80-1.91 (m, 4H), 2.21-2.31 (m, 2H), 2.91-3.11 (m, 4H), 3.40-3.61 (m, 5H).

Workup

  1. concentrationThe reaction was concentrated
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5e55ccbcc042407e996bd56a5e76aa7d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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