3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → 4-Nitrobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester

HRID 1766261Notes

Reaction equation

HRID 1766261 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.[OH-].[Na+]>C1COCC1>[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][S:10]([C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=4)(=[O:11])=[O:12])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 74044-Nitrobenzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 102019314-Nitrobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl esterYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Example 31, using 4-nitrobenzenesulfonyl chloride (997 mg, 4.05 mmol) was added to a mixture of 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (777 mg, 3.4 mmol) in 0.2 N sodium hydroxide (18.6 mL, 3.7 mmol) and THF (20 mL) gave 1.4 g of an orange foam. The product was crystallized from ethyl acetate/hexanes to give 485 mg (35%) of an orange powder. The mother liquors were purified by flash chromatography (silica gel, 5%,7% 2M ammonia in methanol/methylene chloride) to give 800 mg (57%) of the title compound as yellow foam: Total yield was 92%: mp=171-172° C.; MS(m/e): 416 (M+1), 414 (M−1); Calculated for C20H21N3O5S: C, 57.82; H, 5.09; N, 10.11. Found: C, 57.35; H, 4.96; N, 9.88.

Sources & evidence

ORD record
ord-52ef039536054cd6af2430f4294ebf2c
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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