Hydrochloric Acid → HCID 18448550, compound

HRID 32066Notes

Reaction equation

HRID 32066 reaction equation
Cl.CO.C([Si](C)(C)O[CH:10]1[C:19]2[C:14](=[C:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:16]=[CH:17][CH:18]=2)[O:13][CH2:12][CH2:11]1)(C)(C)C.[N-:29]=[N+:30]=[N-:31].[Na+]>CCOCC.CCCCCC.O>[N:29]([CH:10]1[C:19]2[C:14](=[C:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:16]=[CH:17][CH:18]=2)[O:13][CH2:12][CH2:11]1)=[N+:30]=[N-:31]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 33557Sodium AzideHCID 18448551HCID 18448551, compound

Product 1

HCID 18448550HCID 18448550, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

HCl (1.2 mL, 37%) was added to a MeOH (60 mL) solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-chroman-8-ylmethyl]-piperidine (Step C) (3.00 g, 8.30 mmol). After stirring for 1 h, the mixture was evaporated to dryness from benzene. The resulting crude alcohol was dissolved in SOCl2 (5 mL) and stirred for 3 days at RT. Following the removal of the excess SOCl2 in vacuo from hexane, the crude chloride was dissolved in DMF (20 mL) and NaN3 (1.618 g, 24.9 mmol) was added. The mixture was stirred at 80° C. for 1 h and, upon cooling, it was diluted with Et2O (100 mL), hexane (100 mL) and H2O (100 mL). After separation, the organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. MS (APCI+, m/z): 273 (M+1)+.

Workup

  1. customthe mixture was evaporated to dryness from benzene
  2. dissolutionThe resulting crude alcohol was dissolved in SOCl2 (5 mL)
  3. stirringstirred for 3 days at RT
  4. customthe removal of the excess SOCl2 in vacuo from hexane
  5. dissolutionthe crude chloride was dissolved in DMF (20 mL)
  6. stirringThe mixture was stirred at 80° C. for 1 h
  7. temperatureupon cooling
  8. customAfter separation
  9. washthe organic phase was washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4840a7c2bb9443be8f91716e21854c93
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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