Hydrochloric Acid → Ammonia

HRID 2383384Notes

Reaction equation

HRID 2383384 reaction equation
C(OC([N:8]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][N:32]2[CH:36]=[N:35][C:34]([C:37]([OH:50])([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:33]2)[CH2:27][CH2:26]1)C(OC(C)(C)C)=O)=O)(C)(C)C.Cl.CCOCC>C(O)C>[NH3:8].[NH2:8][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][N:32]2[CH:36]=[N:35][C:34]([C:37]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[OH:50])=[N:33]2)[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59145974HCID 59145974, compound

Product 2

HCID 222AmmoniaHCID 59145941HCID 59145941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Di-tert-butyl{9-[4-({3-[hydroxy(diphenyl)methyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}imidodicarbonate (Preparation 27, 1.7 g, 2.46 mmol) was dissolved ethanol (30 ml) and hydrogen chloride in ether (2M, 30 ml, 60 mmol) added. After stirring at room temperature for 18 hours the solvent was removed in vacuo, and the residue partitioned between dichloromethane (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (90:10:1 to 80:20:2, by volume) to furnish the title compound as a white solid, in 60% yield, 725 mg.

Workup

  1. additionadded
  2. customwas removed in vacuo
  3. customthe residue partitioned between dichloromethane (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-af92d56426b2495e95143b02c9b5af2f
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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