N,N,N',N'-Tetramethylmethanediamine → 3-Dimethylaminomethyl-4-chloro-5-benzyloxy-indole

HRID 1898984Notes

Reaction equation

HRID 1898984 reaction equation
C(Cl)(=O)C.CN([CH2:8][N:9]([CH3:11])[CH3:10])C.[Cl:12][C:13]1[C:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2.[OH-].[Na+]>ClCCl>[CH3:11][N:9]([CH2:8][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:21]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:13]=2[Cl:12])[NH:17][CH:16]=1)[CH3:10]

Participants

6

Reactant 4

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 233731004-Chloro-5-benzyloxyindole

Product 1

HCID 233730643-Dimethylaminomethyl-4-chloro-5-benzyloxy-indoleYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (6.42 g, 81.7 mmol) was added dropwise to a stirred solution of bis-dimethylamino-methane (BDAM) (8.34 g, 81.7 mmol) in dry dichloromethane (100 ml), while cooling in an ice bath. After 5 minutes, a solution of 4-chloro-5-benzyloxyindole (15.6 g, 60.7 mmol) in dichloromethane (100 ml) was added, dropwise, followed by addition of 10% aqueous sodium hydroxide (300 ml) after a further 10 minutes. The mixture was extracted with dichloromethane, and the extracts dried (Na2SO4) and stripped to a crude solid which was purified by chromatography (SiO2 ; CHCl3 /MeOH/NH4OH) and recrystallised from ethanol to give 3- dimethylaminomethyl-4-chloro-5-benzyloxyindole (9.66 g), m.p. 137°-9° C.

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialthe extracts dried (Na2SO4)
  4. customwas purified by chromatography (SiO2 ; CHCl3 /MeOH/NH4OH)
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-616bac0ff1de49b380c860efeb52064d
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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