Triethylamine → HCID 21510405, compound

HRID 1577011Notes

Reaction equation

HRID 1577011 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=[O:23].[CH2:27]([C:29]1[CH:37]=[CH:36][C:35]2[NH:34][CH:33]3[CH2:38][CH2:39][NH:40][CH2:41][CH:32]3[C:31]=2[CH:30]=1)[CH3:28]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:7][CH2:8][C:9]([N:40]2[CH2:39][CH2:38][CH:33]3[NH:34][C:35]4[CH:36]=[CH:37][C:29]([CH2:27][CH3:28])=[CH:30][C:31]=4[CH:32]3[CH2:41]2)=[O:11])=[O:23])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 685244-(p-Fluorophenyl)butyric acidHCID 125278768-Ethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 21510405HCID 21510405, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of β-(p-fluorobenzyl)propionic acid (3.0 g) and triethylamine (1.7 g) in dry tetrahydrofuran (90 ml) is added dropwise ethyl chloroformate (1.8 g) under maintaining the temperature of the system at 0° - 2°C. The mixture is stirred at the same temperature for 30 minutes. The mixture is added in portions of 8-ethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (3.3 g) in dry tetrahydrofuran (50 ml) so that the temperature in the system is maintained at 0° - 2°C. After the addition, the mixture is stirred at room temperature for one hour and then refluxed for one hour. After cooling, the precipitated crystals are filtered off and the filtrate is concentrated. The resulting residue is recrystallized from ethanol to give the titled compound (4.2 g), m.p. 120° - 124°C.

Workup

  1. temperatureunder maintaining the temperature of the system at 0° - 2°C
  2. temperatureis maintained at 0° - 2°C
  3. additionAfter the addition
  4. stirringthe mixture is stirred at room temperature for one hour
  5. temperaturerefluxed for one hour
  6. temperatureAfter cooling
  7. filtrationthe precipitated crystals are filtered off
  8. concentrationthe filtrate is concentrated
  9. customThe resulting residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-16356d0ee6ea434aa3a9daa31004f344
Source dataset
uspto-grants-1976_09
Patent number
US03983239

Reaction notes

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