Benzene → HCID 15617948, compound

HRID 1165031Notes

Reaction equation

HRID 1165031 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=O)C1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.C1C=CC=CC=1.[NH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>C(Cl)Cl.CCOCC>[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1)=[O:25]

Participants

7

Reactant 4

HCID 241BenzeneHCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 15617944HCID 15617944, compound

Product 1

HCID 15617948HCID 15617948, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the compound of Example 131 Part B (1.00 g, 3.0 mmole), oxalyl chloride (1.3 mL, 15.0 mmole) and benzene (10 mL) was stirred at room temperature for 21 hours and concentrated under vacuum. The residue was dissolved in methylene chloride (10 mL) and added dropwise to a stirred solution of pyrrolidine (0.53 mL, 6.3 mmole) in methylene chloride (10 mL) at 0°. After 6.5 hours, the mixture was diluted with ether, washed with water and 1.0N hydrochloric acid, then dried over magnesium sulfate and concentrated under vacuum. The crude material was hydrogenated using the procedure of Example 86. Recrystallization of the crude product (ethyl acetate/ethanol) provided the title compound (0.63 g, 76%) as an off-white solid, mp 166°-160°.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in methylene chloride (10 mL)
  3. waitAfter 6.5 hours
  4. washwashed with water and 1.0N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customRecrystallization of the crude product (ethyl acetate/ethanol)

Sources & evidence

ORD record
ord-620c7f1d27ce47bcb2ba208791b34a05
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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