1,4-Dioxane hydrochloride → HCID 58072141, compound

HRID 717074Notes

Reaction equation

HRID 717074 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[C:28]([Si:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[O:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochloride2×HCID 86661577HCID 86661577, compound

Product 1

HCID 58072141HCID 58072141, compoundYield 878.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(tert-butyl-diphenyl-silanyloxy)-piperidine-1-carboxylic acid tert-butyl ester (54 mg, 0.124 mmol) was added 4M HCl/dioxane (2 mL) and CH2Cl2 (5 mL). The reaction mixture was stirred at RT for 2 h. 4M HCl/dioxane (3 mL) added and reaction stirred for a further 1 hr. The reaction mixture was concentrated in vacuo. The crude material was purified by silica gel column chromatography eluting with CH2Cl2 and increasing the polarity to 10% MeOH/CH2Cl2 to obtain 4-(tert-butyl-diphenyl silanyloxy)-piperidine as a cream foam (370 mg, 79%).

Workup

  1. customreaction
  2. stirringstirred for a further 1 hr
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with CH2Cl2
  6. temperatureincreasing the polarity to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-582a07e908b644c2aa10909a878ef3f1
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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