Triethylamine → HCID 18787141, compound

HRID 1107265Notes

Reaction equation

HRID 1107265 reaction equation
[C:1]1([CH:7]([C:15]2[N:19]=[C:18](Cl)[S:17][N:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:21][C:22]1[CH:40]=[CH:39][C:25]([CH:26]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C=O)C>[Cl:21][C:22]1[CH:40]=[CH:39][C:25]([CH:26]([N:33]2[CH2:34][CH2:35][N:36]([C:18]3[S:17][N:16]=[C:15]([CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[O:8][CH:9]4[CH2:14][CH2:13][CH2:12][CH2:11][O:10]4)[N:19]=3)[CH2:37][CH2:38]2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9340NorchlorcyclizineHCID 14763544HCID 14763544, compound

Product 1

HCID 18787141HCID 18787141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[1-phenyl-1-(tetrahydropyran-2-yloxy)methyl]-5-chloro-[1,2,4] thiadiazole (1.56 g, 5.02 mmol) in DMF (25 mL) was added 1-(4-chlorobenzhydryl) piperazine (2.88 g, 10.04 mmol) followed by triethylamine (2.03 g, 20.08 mmol). The resulting mixture was stirred at room temperature for 2 days. Volatile materials were removed in vacuo and the residue was partitionned between dichloromethane and water. The organic layer was collected, dried (sodium sulfate), filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel using a mixture of hexane and ethyl acetate (8/2) thereby affording 1 -[(4-chlorophenyl)phenylmethyl]-4-{3-[phenyl-(tetrahydropyran-2-yloxy)methyl]-[1,2,4]thiadiazol-5-yl}-piperazine (1.90 g, 67%) as a white solid and as a mixture of diastereoisomers. 1H-NMR (CDCl3) δ7.55 (d, J=7.8 Hz, 1H), 7.22-7.39 (m, 13H, Ar--H), 5.89 and 5.85 (s, 0.4H and 0.6H each, αH), 4.90 and 4.64 (t, J=3.2 Hz, 0.4H and 0.6H each, OCHO), 4.29 (m, 1H, CH-Ar), 3.60-4.05 (m, 1H, OCH2), 3.50 (m, 5H, 2CH2 +1H, OCH2), 2.49 (m, 4H, 2CH2), 1.50-1.94 (m, 6H, 3CH2).

Workup

  1. customVolatile materials were removed in vacuo
  2. customThe organic layer was collected
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of hexane and ethyl acetate (8/2)
  8. additionaffording 1 -[(4-chlorophenyl)phenylmethyl]-4-{3-[phenyl-(tetrahydropyran-2-yloxy)methyl]-[1,2,4]thiadiazol-5-yl}-piperazine (1.90 g, 67%) as a white solid and as a mixture of diastereoisomers

Sources & evidence

ORD record
ord-091f212da22f4dcdaf34f0c91843d445
Source dataset
uspto-grants-2000_05
Patent number
US06060472

Reaction notes

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