Acrylamide → HCID 22870342, compound

HRID 975139Notes

Reaction equation

HRID 975139 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[C:17]([NH2:21])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C>COCCOC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH2:19][CH2:18][C:17](=[O:20])[NH2:21]

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 8471TriethylamineHCID 228595901H-Indole, 5-bromo-3-(2-pyrrolidinylmethyl)-, (R)-

Product 1

HCID 22870342HCID 22870342, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 5-bromo-3-(2(R)-pyrrolidinylmethyl)-1H-indole (Preparation 2; 600 mg, 2.1 mmol), acrylamide (168 mg, 2.4 mmol), triethylamine (0.60 ml) and 1,2-dimethoxyethane (11.9 ml), under nitrogen, was heated under reflux for 8 hours, allowed to cool, then partitioned between ethyl acetate (400 ml) and water (400 ml). The organic phase was separated, washed with water (400 ml), dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of 0.880 aqueous ammonia:methanol: dichloromethane (0.1:10:90 to 0.4:10:90), to afford the required product as a foam. Rf 0.26 (SS 7). [α]D25 +59° (c=0.1, CH3OH).

Workup

  1. temperatureunder nitrogen, was heated
  2. temperatureunder reflux for 8 hours
  3. temperatureto cool
  4. custompartitioned between ethyl acetate (400 ml) and water (400 ml)
  5. customThe organic phase was separated
  6. washwashed with water (400 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with a solvent gradient of 0.880 aqueous ammonia:methanol: dichloromethane (0.1:10:90 to 0.4:10:90)

Sources & evidence

ORD record
ord-1e040cb6fa4c4991a90f8312e1726b04
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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