Tert-Butylamine → 4-(2-Hydroxy-3-tert.-butylamino-propoxy)-2-ethoxycarbonyl-6-methylindole

HRID 903916Notes

Reaction equation

HRID 903916 reaction equation
[O:1]1[CH2:20][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][CH2:18][CH3:19])=[O:16])[NH:9]2.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22]>>[OH:1][CH:2]([CH2:20][NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])[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][CH2:18][CH3:19])=[O:16])[NH:9]2

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 205275294-(2,3-Epoxypropoxy)-2-ethoxycarbonyl-6-methyl indole

Product 1

HCID 233355434-(2-Hydroxy-3-tert.-butylamino-propoxy)-2-ethoxycarbonyl-6-methylindoleYield 71%

Procedure

1.7 g 4-(2,3-epoxypropoxy)-2-ethoxycarbonyl-6-methyl-indole are dissolved in 25 ml tert.-butylamine. The solution is stored at room temperature for three days and then evaporated in vacuum. The residue is triturated with ether and aspirated. The crude product is dissolved in hot acetic ester and the solution is mixed with 0.3 ml glacial acetic acid. The precipitate resulting after cooling of the solution is aspirated and dried. There is obtained 1.8 g (~71% of theory) of 4-(2-hydroxy-3-tert.-butylamino-propoxy)-2-ethoxycarbonyl-6-methylindole as acetate; m.p. 181°-183° C.

Workup

  1. customevaporated in vacuum
  2. customThe residue is triturated with ether
  3. dissolutionThe crude product is dissolved in hot acetic ester
  4. additionthe solution is mixed with 0.3 ml glacial acetic acid
  5. customThe precipitate resulting
  6. temperatureafter cooling of the solution
  7. customdried

Sources & evidence

ORD record
ord-19836387e9c64fbdbc345a28c56ffee8
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

Loading…