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Triethylamine → 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

HRID 223244
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 128055024-(4-chloro phenyl)-1-[(3,4-dihydro-4,4-dimethyl-6,7-dimethoxy-1H-2-benzopyran-1-yl)methyl]-1,2,3,6-tetrahydropyridineYield 21%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04352805

Reaction notes

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