Triethylamine → HCID 12805502, compound

HRID 223244Notes

Reaction equation

HRID 223244 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15]Br)[O:8][CH2:7][C:6]2([CH3:18])[CH3:17].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=2)=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH2:31][CH2:30][N:29]([CH2:15][CH:9]3[C:10]4[CH:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[CH:4][C:5]=4[C:6]([CH3:18])([CH3:17])[CH2:7][O:8]3)[CH2:28][CH:27]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridineHCID 205230704,4-Dimethyl-6,7-dimethoxy-1-bromomethylisochroman

Product 1

HCID 12805502HCID 12805502, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.52 g of 6,7-dimethoxy-4,4-dimethyl-1-bromomethylisochroman, 1.35 g of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine, and 2 ml. of triethylamine in 5 ml of DMF are heated at 50° C. for 23 hr. The mixture is partitioned between methylene chloride and aqueous potassium carbonate. The organic phase is dried over sodium sulfate and concentrated. The residue is chromatographed over silica gel utilizing 5% methanol/1/2% ammonium hydroxide/methylene chloride to give a 21% yield 4-(4-chloro phenyl)-1-[(3,4-dihydro-4,4-dimethyl-6,7-dimethoxy-1H-2-benzopyran-1-yl)methyl]-1,2,3,6-tetrahydropyridine.

Workup

  1. customThe mixture is partitioned between methylene chloride and aqueous potassium carbonate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed over silica gel utilizing 5% methanol/1/2% ammonium hydroxide/methylene chloride

Sources & evidence

ORD record
ord-24242943801a4a988b8dccaa11453d43
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

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