HCID 21196159, compound → HCID 21196116, compound

HRID 1066804Notes

Reaction equation

HRID 1066804 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:30])[C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]2)=O)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:30])[C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][CH2:19][N:21]2[CH2:26][CH2:25][CH:24]([N:27]([CH3:28])[CH3:29])[CH2:23][CH2:22]2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:31][CH:32]=1

Participants

3

Reactant 1

HCID 21196159HCID 21196159, compound

Product 1

HCID 21196116HCID 21196116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere around bottom flask is charged with 2-[(4-chlorophenoxy)methyl]-1-methyl-3-[2-[[4-(dimethylamino)piperidin-1-yl]carbonyl]ethyl]-1H-indole (0.194 g, 0.428 mmol). The flask was then placed in an ice bath and boranetetrahydrofuran complex (1.71 ml of a 1.0 M solution in THF, 1.71 mmol) was added. The reaction mixture was then removed from the ice bath and stirred at room temperature for about 90 minutes. The progress of the reaction was monitored by thin layer chromatography. A 1:1 tetrahydrofuran:methanol solution (0.20 ml total) was added, followed by the addition of 2.0 ml of 5.0 N sodium hydroxide.

Workup

  1. customThe flask was then placed in an ice bath
  2. customThe reaction mixture was then removed from the ice bath
  3. additionA 1:1 tetrahydrofuran:methanol solution (0.20 ml total) was added
  4. additionfollowed by the addition of 2.0 ml of 5.0 N sodium hydroxide

Sources & evidence

ORD record
ord-76c4cb00b16c4d3ea2d44c70441d275d
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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