Triethylamine → HCID 18930358, compound

HRID 1736446Notes

Reaction equation

HRID 1736446 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH:21]([C:23]3[C:24]4[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=4[S:26][CH:27]=3)[OH:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[S:26]1[CH:27]=[C:23]([C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:16][CH2:17]2)=[O:22])[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]1=2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18930336HCID 18930336, compound

Product 1

HCID 18930358HCID 18930358, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve oxalyl chloride (4.22 g, 33.28 mmol) in methylene chloride (200 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, dimethylsulfoxide (5.42 g, 69.33 mmol) and stir at -78° C. for 15 minutes. Add, by dropwise addition, a solution of α-[1-(2-phenylethyl)-4piperidinyl]-3-benzo[b]thiophenemethanol (9.75 g, 27.73 mmol) in dimethylsulfoxide (150 mL). Stir at -78° C. for 30 minutes, add triethylamine (15.18 g, 0.150 mol) and stir at -78° C. for 1 hour. Remove the ice bath and stir for an additional 1.5 hours. Evaporate the solvent in vacuo and recrystallize (isopropanol) to give the title compound as a tan powder; mp 110°-112° C.

Workup

  1. additionAdd, by dropwise addition
  2. stirringStir at -78° C. for 30 minutes
  3. stirringstir at -78° C. for 1 hour
  4. customRemove the ice bath
  5. stirringstir for an additional 1.5 hours
  6. customEvaporate the solvent in vacuo
  7. customrecrystallize (isopropanol)

Sources & evidence

ORD record
ord-3c694a246a10479993b40940b1b5d1f0
Source dataset
uspto-grants-1996_07
Patent number
US05541200

Reaction notes

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