Hydrochloric Acid → Hydrochloric Acid

HRID 1738919Notes

Reaction equation

HRID 1738919 reaction equation
[ClH:1].C(OC([N:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:21])[CH3:20])[CH2:14][C@H:13]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=O)C1C=CC=CC=1>>[N+:29]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C@@H:13]2[CH2:14][C@@H:15]([NH:18][C:19](=[O:21])[CH3:20])[CH2:16][CH2:17][NH:12]2)=[CH:28][CH:27]=1)([O-:31])=[O:30].[ClH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53871229HCID 53871229, compound

Product 2

HCID 313Hydrochloric AcidHCID 57118641HCID 57118641, compound

Conditions

Temperature
55 °C

Procedure

Concentrated hydrochloric acid is added to (2R*,4S*)-4-acetylamino-2-(4-nitro-benzyl)-piperidine-1-carboxylic acid benzyl ester (2.65 g, 6.45 mmol) and the mixture is heated at 55° C. for 2 hours, the evolution of gas occurring. The reaction mixture is washed twice with hexane and concentrated by evaporation under reduced pressure using a rotary evaporator. The title compound is obtained as a hydrochloride in the form of white crystals containing 3 molecules of water of crystallisation. M.p.: >250° C. TLC: methylene chloride/methanol/conc. ammonia (90:9:1) Rf =0.29. 1H-NMR (200 MHz, D2O): δ 8.26 (d, 2H), 7.59 (d, 2H), 4.26-4.17 (m,1H), 3.90-3.72 (m, 1H), 3.40-3.02(m, 4H), 1.99 (s, 3H), 2.06-1.75 (m, 4H).

Workup

  1. washThe reaction mixture is washed twice with hexane
  2. concentrationconcentrated by evaporation under reduced pressure
  3. customa rotary evaporator

Sources & evidence

ORD record
ord-e7d30666f85741409c61891f35bbf150
Source dataset
uspto-grants-1999_10
Patent number
US05965562

Reaction notes

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