HCID 57863259, compound → HCID 57863250, compound

HRID 2382989Notes

Reaction equation

HRID 2382989 reaction equation
C([N:8]1[CH2:27][CH2:26][C:11]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C>[CH3:24][N:23]([CH3:25])[C:21]([N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]2([CH2:26][CH2:27][NH:8][CH2:9][CH2:10]2)[CH2:12][CH2:13]1)=[O:22]

Participants

3

Reactant 1

HCID 57863259HCID 57863259, compound

Product 1

HCID 57863250HCID 57863250, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

The crude 1-benzyl-N,N-dimethyl-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1′-carboxamide 2ab (3.1 g, 8.01 mmol) was dissolved in 30 mL absolute ethanol, flushed with nitrogen, and treated with 500 mg of 10% Pd/C. The flask was flushed with nitrogen then fitted with an H2 balloon. The rapidly stirring solution was heated to 45° C. overnight. The reaction was filtered through Celite and concentrated to yield N,N-dimethyl-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1′-carboxamide 2ac as an amber oil. LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 274.2, retention time 1.39 minutes.

Workup

  1. customflushed with nitrogen
  2. additiontreated with 500 mg of 10% Pd/C
  3. customThe flask was flushed with nitrogen
  4. customthen fitted with an H2 balloon
  5. filtrationThe reaction was filtered through Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-70a0ceecc69d45aaa765df37f2e65693
Source dataset
uspto-grants-2012_09
Patent number
US08263605B2

Reaction notes

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