Triethylamine → HCID 53836781, compound

HRID 427336Notes

Reaction equation

HRID 427336 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[NH2:16][C@H:17]1[CH2:26][C:25]2[C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)=[CH:23][CH:22]=[C:21]([Br:40])[C:20]=2[CH2:19][CH2:18]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[Br:40][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:29][CH2:28]2)=[C:25]2[C:20]=1[CH2:19][CH2:18][C@@H:17]([NH:16][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:15][CH:14]=1)[CH2:26]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3452784-(Morpholin-4-yl)benzoic acidHCID 53776853HCID 53776853, compound

Product 1

HCID 53836781HCID 53836781, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

4-Morpholinobenzoic acid (0.50 g, 2.4 mmol; described in: Degutis, J.; Rasteikiene, L.; Degutiene, A. Zh. Org. Khim. 1978, 14(10), 2060-2064) was dissolved in thionyl chloride (10 mL). After 2 min, the thionyl chloride was evaporated in vacuo and the residue was treated with toluene and again the solvent was evaporated in vacuo. Crude acid chloride (81 mg, 0.36 mmol) was dissolved in methylene chloride (10 mL) and added dropwise to a solution of tert-butyl (R)-4-(7-amino-4-bromo-5,6,7,8-tetrahydro-1-naphthyl)piperazin-1-carboxylate (140 mg, 0.34 mmol) and triethylamine (71 μL, 0.51 mmol) in methylene chloride (10 mL). After the addition, the reaction was stirred at ambient temperature for 15 min and was then washed with a diluted aqueous solution of sodium hydrogen carbonate and the phases were separated. The organic phase was dried (Na2SO4), filtered and evaporated in vacuo and the residue was purified on a silica gel column using chloroform/ethanol saturated with NH3 (100:2) as the eluent. Yield: 160 mg (79%) of a viscous colorless oil: [α]21D−11° (c=1, chloroform); TSPMS m/z (relative intensity) 599 and 601 (35, M++1).

Workup

  1. customthe thionyl chloride was evaporated in vacuo
  2. additionthe residue was treated with toluene
  3. customagain the solvent was evaporated in vacuo
  4. additionAfter the addition
  5. washwas then washed with a diluted aqueous solution of sodium hydrogen carbonate
  6. customthe phases were separated
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-9cd08c53562c401696defdffba758d56
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

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