Hydrochloric Acid → HCID 62342453, compound

HRID 1524084Notes

Reaction equation

HRID 1524084 reaction equation
[Br:1][C:2]1[C:3]([O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[NH4+].[OH-]>CO>[Br:1][C:2]1[C:3]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 58547976HCID 58547976, compound

Product 1

HCID 62342453HCID 62342453, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-((3-bromopyridin-2-yl)oxy)piperidine-1-carboxylate in MeOH (10 mL) was added HCl (2 mL, 1 N). The reaction mixture was stirred at rt for 2 h before adjusting the pH to ˜9 with NH4OH. The mixture was then concentrated to dryness and the crude product purified by FCC to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.17 (dd, J=4.8, 1.7, 1H), 8.06 (dd, J=7.7, 1.7, 1H), 6.98 (dd, J=7.7, 4.9, 1H), 5.31 (m, 1H), 3.18-3.07 (m, 4H), 2.22-2.05 (m, 2H), 1.92 (m, 2H).

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. customthe crude product purified by FCC

Sources & evidence

ORD record
ord-4463974a5d904702a2e7d04f9bcc589e
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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