Tert-Butylamine → HCID 23335502, compound

HRID 903922Notes

Reaction equation

HRID 903922 reaction equation
[O:1]1[CH2:18][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:15](=[O:17])[NH2:16])[NH:9]2.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20]>>[OH:1][CH:2]([CH2:18][NH:23][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:3][O:4][C:5]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:15](=[O:17])[NH2:16])[NH:9]2

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 23335530HCID 23335530, compound

Product 1

HCID 23335502HCID 23335502, compoundYield 55%

Procedure

1.5 g of 4-(2,3-epoxypropoxy)-2-carbamoyl-6-methyl indole in 25 ml tert.-butylamine is heated to boiling for 24 hours. The solution is then evaporated and the residue dissolved in chloroform. The chloroform solution is washed with water, dried and evaporated. The residue is suspended in hot acetic ester and mixed with 0.8 g benzoic acid. A clear solution will result here, from which a precipitate deposits. This is aspirated and recrystallized from 100 ml acetic ester. There is obtained 1.5 g (55% of theory) 4-(2-hydroxy-3-tert.-butylaminopropoxy)-2-carbamoyl-6-methyl indole as benzoate; m.p. 213°-214° C.

Workup

  1. customThe solution is then evaporated
  2. dissolutionthe residue dissolved in chloroform
  3. washThe chloroform solution is washed with water
  4. customdried
  5. customevaporated
  6. additionmixed with 0.8 g benzoic acid
  7. customA clear solution will result here, from which a precipitate deposits
  8. customThis is aspirated and recrystallized from 100 ml acetic ester

Sources & evidence

ORD record
ord-d5b4616308f64dc4a93e5e2d5e6b4f82
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

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