Hydrochloric Acid → HCID 67543554, compound

HRID 1809793Notes

Reaction equation

HRID 1809793 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[C:19]3[O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:18]=3[CH:17]=[CH:16][CH:15]=2)[C@@H:10]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH2:9]1)=O)(C)(C)C.[ClH:41]>>[ClH:41].[C:32]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:31]=[CH:30][C:29]([CH2:28][O:27][C@@H:10]2[C@@H:11]([C:14]3[C:19]4[O:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[C:18]=4[CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67542408HCID 67542408, compound

Product 1

HCID 67543554HCID 67543554, compound

Procedure

A mixture of (3R*,4R*)-3-(biphenyl-4-ylmethoxy)-4-dibenzofuran-4-yl-piperidine-1-carboxylic acid t-butyl ester (prepared analogously as described in Example 1; 218 mg, 0.41 mmol) and HCl (5M in 2-propanol, 2 mL, 10 mmol) is stirred for 1 h at RT. The solvent is removed in vacuo, the residue triturated with hot MeOH and the suspension filtered. The filter cake is washed with MeOH and ether and dried at 60° C. in vacuo to afford (3R*,4R*)-3-(biphenyl-4-ylmethoxy)-4-dibenzofuran-4-yl-piperidine hydrochloride: MS 434.6 [M+H]+; Rf 0.23 (DCM/MeOH 9:1).

Workup

  1. customprepared analogously
  2. customThe solvent is removed in vacuo
  3. customthe residue triturated with hot MeOH
  4. filtrationthe suspension filtered
  5. washThe filter cake is washed with MeOH and ether
  6. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-ffde54b1ac0244f9b1b4106a527f2720
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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