Hydrochloric Acid → HCID 22128388, compound

HRID 1004952Notes

Reaction equation

HRID 1004952 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH:11]3[O:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[ClH:35]>CO>[ClH:35].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH:11]3[O:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53909146HCID 53909146, compound

Product 1

HCID 22128388HCID 22128388, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 190 mg (0.41 mmol) of tert-butyl (3RS,4RS)-4-benzo[1,3]dioxol-5-yl-3-(naphthalen-2-ylmethoxy)-piperidine-1 -carboxylate in a mixture of 5 ml of methanol and 25% aqueous hydrochloric acid was heated under reflux for 1 hour. Subsequently, the solvent mixture was distilled off under reduced pressure. After recrystallization of the residue from a mixture of methanol and ether there were obtained 130 mg (73% of theory) of (3RS,4RS)-4-(1,3-benzodioxol-5-yl)-3-naphthalen-2-ylmethoxy-piperidine hydrochloride as a white powder; MS: 362 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. distillationSubsequently, the solvent mixture was distilled off under reduced pressure
  4. customAfter recrystallization of the residue
  5. additionfrom a mixture of methanol

Sources & evidence

ORD record
ord-d30a36ed34a5473b86469d4fe9240b1d
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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