Methylamine → 4'-(Methylamino)spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 49626Notes

Reaction equation

HRID 49626 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[O:8][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[CH2:10][C:3]=12.[CH3:18][NH2:19]>>[CH3:18][NH:19][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[O:8][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[CH2:10][C:3]=12

Participants

3

Reactant 2

HCID 6329MethylamineHCID 100377734'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

Product 1

HCID 220458494'-(Methylamino)spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

Procedure

A solution of 151 mg (0.60 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 25 mL of 40% aqueous methylamine was heated to 175° C. in a steel bomb for 18 hours, then cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in 10 mL of ethanol containing 0.4 mL of concentrated hydrochloric acid and the solution was allowed to stand overnight. After filtering, the solution was concentrated in vacuo and the residue crystallized from isopropanol, giving 147 mg of the title compound as a white solid: electrospray MS (m/z, relative intensity) 246 ([MH]+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 10 mL of ethanol containing 0.4 mL of concentrated hydrochloric acid
  3. filtrationAfter filtering
  4. concentrationthe solution was concentrated in vacuo
  5. customthe residue crystallized from isopropanol

Sources & evidence

ORD record
ord-fdabf487771d48f2a84bace42728fd05
Source dataset
uspto-grants-2004_03
Patent number
US06706878B2

Reaction notes

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