Hydrochloric Acid → HCID 86635427, compound

HRID 599470Notes

Reaction equation

HRID 599470 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([OH:25])=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:30]>O1CCOCC1>[ClH:30].[C:26]([C:17]1[CH:16]=[C:15]([S:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]=1[OH:25])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866354264-(3,5-Di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86635427HCID 86635427, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (Ex. 3b, 21 g, 50 mmol) in a 250 mL round bottom flask was added 100 mL of a 4 N HCl in dioxane. The mixture was stirred at room temperature for 5 h and concentrated under reduced pressure to about 25 mL. The solid was collected through filtration, washed with Ethyl acetate/hexanes (1:2 v/v, 50 mL), and dried under high vacuum to afford 2,6-di-tert-butyl-4-(piperidin-4-ylsulfanyl)-phenol hydrochloride as a white solid (16 g, 97%). 1H NMR (400 MHz, CD3OD): δ 7.26 (s, 2H), 3.35 (m, 2H), 3.10 (m, 1H), 3.00 (m, 2H), 2.11 (m, 2H), 1.68 (m, 2H), 1.37 (s, 18H). ESI/CI-MS m/z 322 ([M+H]+), 320 ([M−H]−). HRMS (ESI) Calcd. for C19H32ClNOS: 321.2126 (M+). Found: 321.2127. Anal. Calcd. for C19H32ClNOS, C, 63.75; H, 9.01; N, 3.91; S, 8.96. Found: C, 63.43; H, 9.08; N, 3.94; S, 8.72.

Workup

  1. concentrationconcentrated under reduced pressure to about 25 mL
  2. filtrationThe solid was collected through filtration
  3. washwashed with Ethyl acetate/hexanes (1:2 v/v, 50 mL)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-62922374bb3c4080a287c9b190530fcc
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

Loading…