Dimethylformamide → HCID 22716807, compound

HRID 1583044Notes

Reaction equation

HRID 1583044 reaction equation
C(N([CH:7]([CH3:9])[CH3:8])CC)(C)C.CS(O[CH2:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:19]=[O:20])(=O)=O.[CH3:32][N:33]([CH3:36])C=O>>[C:26]1([CH2:25][O:24][C:23]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][C:16]=2[CH2:15][N:33]2[CH2:36][CH2:19][CH:18]([CH2:21][C:8]3[CH:7]=[CH:9][CH:23]=[CH:16][CH:15]=3)[CH2:17][CH2:32]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 21957468[2-(Benzyloxy)-5-formylphenyl]methyl methanesulfonate

Product 1

HCID 22716807HCID 22716807, compound

Procedure

To a solution of 4-(phenylmethyl)piperidinyl (200 mg) and diisopropylethylamine (130 mg) in dimethylformamide (1 ml) was added 3-[[(methylsulfonyl)oxy]methyl]-4-phenylmethoxybenzaldehyde (320 mg). After stirring at room temperature for 3 hours the reaction mixture was partially concentrated under reduced pressure and the residue was purified by flash column chromatography using petroleum ether:diethyl ether (1:1) as eluant. The pure fractions were combined and evaporated under reduced pressure to give 4-phenylmethoxy-3-[[4-(phenylmethyl)-1-piperidinyl]-methyl]benzaldehyde (170 mg) as a gum. 1H NMR (CDCl3) δ9.95 (s, 1H, CHO); 5.20 (s, 2H); 3.68 (s, 2H). TLC (silica gel): Rf=0.2 (dichloromethane: diethyl ether, 3:1).

Workup

  1. concentrationwas partially concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7c8dda3035b6436294696310883df09f
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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