Hydrochloric Acid → Ammonia

HRID 2383365Notes

Reaction equation

HRID 2383365 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]([CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)([OH:44])[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.C(OCC)C>ClCCl>[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[CH2:26][CH2:27][CH:28]([CH2:31][N:32]2[CH:36]=[N:35][C:34]([C@@:37]([CH:45]3[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]3)([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[OH:44])=[N:33]2)[CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59145968Di-tert-butyl{9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperdin-1-yl]nonyl}imidodicarbonate

Product 2

HCID 222AmmoniaHCID 59145972(R)-(1-{[1-(9-aminononyl)piperidin-4-yl]methyl}-1H-1,2,4-triazol-3-yl)(cyclohexyl) phenylmethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl{9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperdin-1-yl]nonyl}imidodicarbonate (Preparation 5, 2.6 g, 3.7 mmol) was dissolved in dichloromethane (15 ml) and hydrogen chloride in diethylether (2M, 15 ml, 30 mmol) added. After stirring at room temperature for 5 hours the solvent was removed in vacuo, the residue was 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 (97.5:2.5:0.25, by volume) to furnish the title compound as a clear oil, in 70% yield, 1.29 g (contains 10% of other triazole regio-isomer).

Workup

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

Sources & evidence

ORD record
ord-38e3ba30746a47c5b598f07b623da761
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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