Benzyl Bromide → HCID 19697528, compound

HRID 863227Notes

Reaction equation

HRID 863227 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([OH:13])=[O:12])[CH2:2]1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:14]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([O:13][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:12])[CH2:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 139310661,2,3,4-Tetrahydroquinoline-3-carboxylic acid

Product 1

HCID 19697528HCID 19697528, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.6 g of 1,2,3,4-tetrahydroquinoline-3(R,S)-carboxylic acid (Example 1t)) are stirred in 100 ml of dimethylformamide, with the addition of 12.7 ml of benzyl bromide and 25.1 g of caesium carbonate, at room temperature for 24 h. The concentrated crude product is then purified by means of FC over 250 g of silica gel with a 1:1 mixture of methylene chloride and hexane as the mobile phase. The title compound is obtained: Rf (1:1 mixture of methylene chloride and hexane)=0.31.

Workup

  1. concentrationThe concentrated crude product
  2. customis then purified by means of FC over 250 g of silica gel with a 1:1 mixture of methylene chloride and hexane as the mobile phase

Sources & evidence

ORD record
ord-4fb48e95b0ac4263a4c40d34be82b20f
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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