Diisopropylamine → 4-Chloro-5,6,7,8-tetrahydro-8-(phenylseleno)quinoline

HRID 1613590Notes

Reaction equation

HRID 1613590 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[Cl:19][C:20]1[C:29]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[N:23]=[CH:22][CH:21]=1.[C:30]1([Se:36]Cl)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[Cl:19][C:20]1[C:29]2[CH2:28][CH2:27][CH2:26][CH:25]([Se:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]=2[N:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8058HexaneHCID 21928ChloroselenobenzeneHCID 109428314-Chloro-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Product 1

HCID 148359614-Chloro-5,6,7,8-tetrahydro-8-(phenylseleno)quinolineYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of diisopropylamine (18.5 ml, 132 mmol) in tetrahydrofuran (100 ml) at 0° was treated with 1.5M butyllithium solution in hexane (88 ml, 132 mmol) under an atmosphere of nitrogen, stirred for 10 min, cooled to -78°, treated dropwise with the product of Step 2 (7.35 g, 44 mmol) in tetrahydrofuran (50 ml) at <-65°, stirred at -78° for 20 min, treated with phenylselenyl chloride (8.5 g, 44 mmol) in tetrahydrofuran (50 ml), warmed to room temperature, and quenched with saturated aqueous ammonium chloride (250 ml). The reaction was worked-up in a similar way to that described in Example 25, Step 1 and the product (9 g) isolated by chromatography [silica; hexane-ether (2:1)] as an oil.

Workup

  1. temperaturecooled to -78°
  2. stirringstirred at -78° for 20 min
  3. customquenched with saturated aqueous ammonium chloride (250 ml)

Sources & evidence

ORD record
ord-37262a8217874791a2961144e6346e22
Source dataset
uspto-grants-1993_03
Patent number
US05194439

Reaction notes

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