Morpholine → HCID 22735232, compound

HRID 1279218Notes

Reaction equation

HRID 1279218 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=2)[N:4]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(O)C>[N:17]1([CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=3)[N:4]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22735234HCID 22735234, compound

Product 1

HCID 22735232HCID 22735232, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(Morpholin-4-ylmethyl)-6-trifluoro-methylquinoline may be prepared by carrying out the procedure as in Example 29, but starting with 3 g of 2-chloromethyl-6-trifluoromethylquinoline and 3.18 g of morpholine in 30 ml of ethanol. The crude product obtained is chromatographed on a silica gel column, eluting with a mixture of dichloromethane and methanol (97.5-2.5 by volume). 3.5 g of 2-(morpholin-4-yl-methyl)-6-trifluoromethylquinoline are thus obtained in the form of an orange-coloured oil [1H NMR spectrum in CDCl3, T=300K, δ in ppm (300 MHz): 2.55 (4H, m, 2 NCH2), 3.75 (4H, m, 2 OCH2), 3.85 (2H, s, NCH2), 7.75 (1H, d, J=8 Hz, arom. CH), 7.85 (1H, dd, J=8 and 2 Hz, arom. CH), between 8.10 and 8.25 (3H, m, 3arom. CH)].

Workup

  1. customThe crude product obtained
  2. customis chromatographed on a silica gel column
  3. washeluting with a mixture of dichloromethane and methanol (97.5-2.5 by volume)

Sources & evidence

ORD record
ord-be1088f1fb5642a88e2713c361b88fdc
Source dataset
uspto-grants-2002_09
Patent number
US06448241B1

Reaction notes

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