Pyridinium chloride → HCID 69431066, compound

HRID 1766228Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([CH3:13])[CH:7]=[C:6]2[CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.Cl.N1C=CC=CC=1>>[CH3:13][N:8]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[CH:11][C:10]=2[CH3:12])[C:6]([CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:7]1

Participants

Reactant 2

HCID 10176127Pyridinium chloride

HCID 69435813HCID 69435813, compound

Product 1

HCID 69431066HCID 69431066, compoundYield 92%

Procedure

By a method similar to Preparation 8, using 5-methoxy-1,7 dimethyl-3-(1-methylpiperdin-4-yl)-1H-indole (1.53 g) and pyridine hydrochloride (25 g) to afford 1.33 g (92%) of the title compound: mass spectrum (ion spray): m/z=259 (M+1); 1H NMR (DMSOd6): 8.47 (s, 1H), 6.81 (s, 1H), 6.62 (d, J=2.20 Hz, 1H), 6.33 (d, J=1.46 Hz, 1H), 3.88 (s, 3H), 2.82 (m, 2H), 2.53-2.46 (m, 4H), 2.19 (s, 3H), 1.99 (m, 2H), 1.84 (m, 2H), 1.64 (m, 1H), 1.56 (m, 1H); Calculated for C16H22N2O-0.6 H2O: C, 71.39; H, 8.69; N, 10.41. Found: C, 71.39; H, 8.31; N, 10.33.

Workup

customBy a method similar to Preparation 8

Sources & evidence

ORD record: ord-a7556156c654465290748590cfd3f049
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230011B2

Reaction notes

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