Triethylamine → HCID 89422984, compound

HRID 1481749Notes

Reaction equation

HRID 1481749 reaction equation
[C:1]([C:6]1[CH:14]=[CH:13][C:12]2[N:11]3[CH2:15][CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C:10]3=[CH:9][C:8]=2[CH:7]=1)(=O)[CH2:2][CH2:3][CH3:4].[CH3:26][O:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31].CCN(CC)CC>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:22]([O:21][C:19]([N:17]1[CH2:16][CH2:15][N:11]2[C:12]3[CH:13]=[CH:14][C:6]([C:1](=[N:31][CH2:30][C:29]4[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:28]=4[O:27][CH3:26])[CH2:2][CH2:3][CH3:4])=[CH:7][C:8]=3[CH:9]=[C:10]2[CH2:18]1)=[O:20])([CH3:24])([CH3:23])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 71284792HCID 71284792, compound

Product 1

HCID 89422984HCID 89422984, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 8-butyryl-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate (1.0 g, 2.9 mmol) in CH2Cl2 (20 mL), cooled to 0° C., was added 2,4-dimethoxybenzyl amine (0.5 mL, 3.2 mmol) and Et3N (1.2 mL, 9 mmol). To this mixture was added a solution of TiCl4 (1.8 mL, 1M, 1.8 mmol) in CH2Cl2 dropwise via an addition funnel. Upon completion of addition, the reaction was stirred at room temperature for 6 h before it was quenched with a saturated solution of NaHCO3. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered, and concentrated to give a crude product that was used immediately without further purification.

Workup

  1. additionUpon completion of addition
  2. customwas quenched with a saturated solution of NaHCO3
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec0b604fa4e641989d09771c197cd1b4
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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