Triethylamine → HCID 14219688, compound

HRID 980449Notes

Reaction equation

HRID 980449 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:5]=1[N:6]2[CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15].C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(#N)C.C(OCC)C>[CH3:15][N:14]([CH3:16])[CH2:13][CH2:12][CH2:11][N:6]1[C:7]2[C:3](=[C:2]([NH:1][C:31](=[O:32])[O:33][CH2:34][CH3:35])[CH:10]=[CH:9][CH:8]=2)[C:4]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:5]1=2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13533652HCID 13533652, compound

Product 1

HCID 14219688HCID 14219688, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-amino-5-(3-dimethylaminopropyl)-6,7,8,9,10,11-hexahydro-5H-cyclooct[b]indole (5 g, 0.024 mol) and 5 mL of triethylamine in 80 mL dry acetonitrile (under nitrogen), stirred and kept below 20° C., was added 5 mL ethyl chloroformate. The reaction mixture was stirred at 25°-28° C. for 18 hours. The mixture was diluted with diethyl ether and the precipitate (Et3N.HCl) was filtered off and washed with diethyl ether. The filtrate was dried over sodium sulfate, filtered and the filtrate treated with dry hydrogen chloride. On standing a blueish solid separated. This was filtered, washed with diethyl ether, and dried in a vacuum pistol. There was obtained 1.15 g of the title compound as the hydrochloride.

Workup

  1. customkept below 20° C.
  2. filtrationthe precipitate (Et3N.HCl) was filtered off
  3. washwashed with diethyl ether
  4. dry with materialThe filtrate was dried over sodium sulfate
  5. filtrationfiltered
  6. additionthe filtrate treated with dry hydrogen chloride
  7. customseparated
  8. filtrationThis was filtered
  9. washwashed with diethyl ether
  10. customdried in a vacuum pistol

Sources & evidence

ORD record
ord-a8e20324201a47b09f60485b4b3dec8a
Source dataset
uspto-grants-1987_01
Patent number
US04638008

Reaction notes

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