N-Methylbenzylamine → HCID 54549073, compound

HRID 975160Notes

Reaction equation

HRID 975160 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[CH3:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:19]([N:18]([CH3:17])[C:1](=[O:5])[C:2]([C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([Br:7])[CH:9]=2)[NH:13][CH:12]=1)=[O:3])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 249055-BromoindoleHCID 65578Oxalyl chloride

Product 1

HCID 54549073HCID 54549073, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Oxalyl chloride (2.24 ml, 25 mmol) was added dropwise to a stirred solution of 5-bromoindole (5.0 g, 25 mmol) in anhydrous tetrahydrofuran (60 ml) under nitrogen at room temperature. After 2 hours the reaction mixture was ice-cooled and a solution of N-methylbenzylamine (10.8 g, 89 mmol) in anhydrous tetrahydrofuran (15 ml) added dropwise, then the resulting mixture was stirred for a further 2 hours at 0°-5° C. and partitioned between ethyl acetate and 2M hydrochloric acid. The organic phase was washed with 2M hydrochloric acid and then water, dried (Na2SO4) and evaporated under reduced pressure to give a solid which was triturated with a 1:2 mixture of hexane:ether, washed with ether (×3) and dried in vacuo, to afford the required product (7.02 g) as a solid. Rf 0.60 (SS 7). Found: C,57.65; H,4.02; N,7.50. C18H15BrN2O2 ; 0.33 H2O requires C,57.30; H,4.16; N,7.42%.

Workup

  1. temperatureice-cooled
  2. custompartitioned between ethyl acetate and 2M hydrochloric acid
  3. washThe organic phase was washed with 2M hydrochloric acid
  4. dry with materialwater, dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto give a solid which
  7. customwas triturated with a 1:2 mixture of hexane
  8. washether, washed with ether (×3)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-f358b48bf2514b03956cc67c227acaf5
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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