HCID 69422567, compound → HCID 69419848, compound

HRID 1178871Notes

Reaction equation

HRID 1178871 reaction equation
[ClH:1].C(OC([CH2:9][NH:10][C@H:11]1[CH2:15][CH2:14][C@@H:13]([N:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:12]1)=O)(C)(C)C>Cl.CO>[ClH:1].[ClH:1].[CH3:9][NH:10][C@H:11]1[CH2:15][CH2:14][C@@H:13]([N:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:12]1

Participants

4

Reactant 1

HCID 69422567HCID 69422567, compound

Product 1

HCID 69419848HCID 69419848, compoundYield 184.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

cis-1-[(tert-Butyloxycarbonyl)methylamino]-3-(4-methylpiperidin-1-yl)cyclopentane hydrochloride (394.5 mg, 1.19 mmol) was dissolved in hydrogen chloride in methanol [prepared by cautious addition of acetyl chloride (2 ml) to methanol (20 ml)]. The resulting solution was stirred at room temperature for 3 hours, concentrated in vacuo to give an oil which was crystalized from methanol-ethyl acetate. The solid was collected under suction, washed with ethyl acetate and dried in vacuo to give the title compound (295.3 mg, 93%) as a white solid; δH (400 MHz, CD3OD) 1.02 (3H, d, J 6.4 Hz), 1.51-1.63 (2H, m), 1.73 (1H, m), 1.92-2.29 (7H, m), 2.67 (1H, m), 2.73 (3H, s), 2.98 (2H, m), 3.62 (4H, m); m/z (ES+) 197 ([M+H]+, 100%), 166.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give an oil which
  3. customwas crystalized from methanol-ethyl acetate
  4. customThe solid was collected under suction
  5. washwashed with ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-15e860296a8b430997f77529cdf1cd24
Source dataset
uspto-grants-2007_10
Patent number
US07276607B2

Reaction notes

Loading…