Hydrochloric Acid → 4-(2,3-dihydro-1H-isoindol-5-yl)-1-methyl-piperidin-4-ol dihydrochloride

HRID 424098Notes

Reaction equation

HRID 424098 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3([OH:24])[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.[ClH:25]>C1COCC1>[ClH:25].[ClH:25].[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([C:17]3([OH:24])[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:12][CH:11]=2)[CH2:16][NH:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666723445-(4-Hydroxy-1-methyl-piperidin-4-yl)-1,3-dihydroisoindole-2-carboxylic acid tert-butyl ester

Product 1

HCID 666725264-(2,3-dihydro-1H-isoindol-5-yl)-1-methyl-piperidin-4-ol dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-hydroxy-1-methyl-piperidin-4-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (107 mg; 0.32 mmol) in THF (4 ml) was treated with concentrated hydrochloric acid (1.5 ml) then heated at reflux for 4 hours, then evaporated and re-evaporated with toluene to give 4-(2,3-dihydro-1H-isoindol-5-yl)-1-methyl-piperidin-4-ol dihydrochloride as a brown gum.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 4 hours
  3. customevaporated
  4. customre-evaporated with toluene

Sources & evidence

ORD record
ord-e03c9de76a5f4fe986fff748d8b5cbb7
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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