Hydrochloric Acid → HCID 22628386, compound

HRID 278415Notes

Reaction equation

HRID 278415 reaction equation
[OH:1][C:2]1([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[CH2:7][CH2:6][N:5]([CH2:8][CH:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:18])[CH:15]=3)[CH:10]2O)[CH2:4][CH2:3]1.Cl.O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[OH:18][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[C:9]([CH2:8][N:5]3[CH2:6][CH2:7][C:2]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)([OH:1])[CH2:3][CH2:4]3)[CH2:17]2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 22628407HCID 22628407, compound

Product 1

HCID 22628386HCID 22628386, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(1RS,2RS) and (1RS, 2SR)-2-[4-hydroxy-4-(4-methyl-benzyl)-piperidine-1-ylmethyl]-indan-1,5-diol (310 mg, 0.84 mmol) and ethanolic HCl (5 eq.) was heated in EtOAc (30 ml) at 65° C. for 1.5 hr. Distilled H2O (30 ml) and 10% NaHCO3 (30 ml) was added and the mixture shaken, the aqueous phase was further extracted with EtOAc (2×20 ml) and the combined organic extracts were washed with satd. NaCl solution (30 ml), dried (Na2SO4) and filtered. Evaporation of the solvent afforded 1-(6-hydroxy-1H-inden-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol as a beige solid (308 mg, 0.84 mmol, 100%) Mp. 154-157° C., MS m/e=350.2 (M+H+).

Workup

  1. extractionthe aqueous phase was further extracted with EtOAc (2×20 ml)
  2. washthe combined organic extracts were washed with satd
  3. dry with materialNaCl solution (30 ml), dried (Na2SO4)
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2b1d54beeee9405b9b814ad0b400c9fc
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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