1-Methyl-4-(methylamino)piperidine → HCID 68773722, compound

HRID 1174530Notes

Reaction equation

HRID 1174530 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]([OH:13])=O.[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21][CH3:22])[CH2:17][CH2:16]1>ClCCl>[CH3:22][N:21]([CH:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[C:11]([C:7]1[C:6]2[C:10](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[NH:9][CH:8]=1)=[O:13]

Participants

4

Reactant 2

HCID 5663231-Methyl-4-(methylamino)piperidineHCID 248204637-Bromo-1H-indole-3-carboxylic acid

Product 1

HCID 68773722HCID 68773722, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-Bromo-1H-indole-3-carboxylic acid (A) (240 mg, 1 mmol) in dichloromethane (8 cm3) was added polystyrene-bound carbodiimide (1 g, loading 1.3 mmol/g, 1.3 mmol) followed by 1-methyl-4-(methylamino)piperidine (192 mg, 1.5 mmol) and the resulting suspension was gently shaken at room temperature for 16 h. The suspension was filtered and the resin washed with dichloromethane. The filtrate was then washed with saturated aqueous sodium bicarbonate solution, water before the organic portion was dried over magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to give the title compound (B) (107.2 mg, 31%).

Workup

  1. filtrationThe suspension was filtered
  2. washthe resin washed with dichloromethane
  3. washThe filtrate was then washed with saturated aqueous sodium bicarbonate solution, water before the organic portion
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-be51d278a8604309ae528b77a2598c14
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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