Indole → HCID 9817415, compound

HRID 988098Notes

Reaction equation

HRID 988098 reaction equation
N1C2C(=CC=CC=2)C=C1.Br[C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][N:17]2[CH:20]2CCC[CH2:23][N:22]([CH3:27])[CH2:21]2)=[CH:13][CH:12]=1.BrC1C=C2C(C=CN2S(C)(=O)=[O:39])=CC=1.CN1C[CH2:47][CH2:46][CH2:45][CH:44]1[CH2:49][OH:50].[H-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[OH:39][C:45]1([C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[CH:16][N:17]3[CH2:20][CH2:21][N:22]([CH3:23])[CH3:27])=[CH:13][CH:12]=2)[CH2:44][CH2:49][O:50][CH2:47][CH2:46]1

Participants

8

Reactant 6

HCID 798IndoleHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 893941-Methyl-2-piperidinemethanolHCID 18007495HCID 18007495, compoundHCID 18007612HCID 18007612, compound

Product 1

HCID 9817415HCID 9817415, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Bromo-1-(N-methylpiperidin-2-yl)methyl)-1H-indole (220 mg, 57.2%) and 6-bromo-1-(N-methyl-azepan-3-yl)-1H-indole (94 mg, 24.4%); from 6-bromo-1-methanesulfonyl-1H-indole (344 mg, 1.25 mmol) and N-methylpiperidine-2-methanol (395 mg, 2.5 mmol) with NaH (53 mg, 2.2 mmol) and potassium carbonate (325 mg, 2.35 mmol) in toluene (10 mL) at 100° C. overnight.

Workup

  1. customat 100° C.
  2. customovernight

Sources & evidence

ORD record
ord-d747f9622d5044e0ab703af6bd9cc1b2
Source dataset
uspto-grants-2003_10
Patent number
US06635639B2

Reaction notes

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