Triethylamine → HCID 76819802, compound

HRID 537745Notes

Reaction equation

HRID 537745 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13](O)=[O:14])[C:10]2([C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:31]1([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]([N:40]2[CH2:39][CH2:38][CH:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:42][CH2:41]2)=[O:14])[C:10]2([C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 698734-PhenylpiperidineHCID 57496437HCID 57496437, compound

Product 1

HCID 76819802HCID 76819802, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

N-benzyl-3,4-dihydro-2H-spiro[naphthalene-1,3′-pyrrolidine]-4′-carboxylic acid (0.1 g, 0.311 mmol) in CH2Cl2 (4 ml) was added oxalyl chloride (0.187 ml, 0.373 mmol) followed by 2 drops of DMF. Stirred at room temperature for 30 minutes and concentrated. Dissolve in THF (5 mL) and added 4-phenylpiperidine (0.050 g, 0.311 mmol) and triethylamine (0.173 ml, 1.245 mmol).

Workup

  1. concentrationconcentrated
  2. dissolutionDissolve in THF (5 mL)

Sources & evidence

ORD record
ord-44de770b782b469dbcf02b08c54937b0
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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