Hydrochloric Acid → HCID 70896253, compound

HRID 2369870Notes

Reaction equation

HRID 2369870 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([N:9]1[CH2:22][CH2:21][CH2:20][N:18]3[C:19]4[C:15]([CH:16]=[CH:17]3)=[CH:14][CH:13]=[CH:12][C:11]=4[C:10]1=[O:23])[CH2:2]2.[ClH:24]>CO>[ClH:24].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([N:9]1[CH2:22][CH2:21][CH2:20][N:18]3[C:19]4[C:15]([CH:16]=[CH:17]3)=[CH:14][CH:13]=[CH:12][C:11]=4[C:10]1=[O:23])[CH2:2]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69937553HCID 69937553, compound

Product 1

HCID 70896253HCID 70896253, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (R)-2-(quinuclidin-3-yl)-2,3,4,5-tetrahydro-1H-[1,5]diazocino[3,2,1-hi]indol-1-one (127 mg, 0.4 mmol) from Step E above in methanol was added HCl (1.25 M in methanol) and the solution was concentrated under reduced pressure to give (R)-2-(quinuclidin-3-yl)-2,3,4,5-tetrahydro-1H-[1,5]diazocino[3,2,1-hi]indol-1-one hydrochloride (124 mg, 88%) as an off-white solid: 1H NMR (500 MHz, D2O) δ 7.76 (d, J=8.0 Hz, 1H), 7.32 (d, J=7.5 Hz, 1H), 7.24 (d, J=3.0 Hz, 1H), 7.16 (t, J=7.5 Hz, 1H), 6.57 (d, J=3.5 Hz, 1H), 4.31-4.22 (m, 2H), 4.19-4.10 (m, 1H), 3.97-3.90 (m, 1H), 3.84-3.66 (m, 2H), 3.62-3.48 (m, 2H), 3.47-3.22 (m, 4H), 2.58-2.47 (m, 1H), 2.24-1.80 (m, 5H); MS (ESI+) m/z 310 (M+H).

Workup

  1. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bd6f1eb60a2e4647b5f0e45fcafbf53d
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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