Acetyl chloride → HCID 67131297, compound

HRID 2382988Notes

Reaction equation

HRID 2382988 reaction equation
[CH2:1]([N:8]1[CH2:22][CH2:21][C:11]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:22][CH2:21][C:11]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:28](=[O:30])[CH3:29])[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 57567372873056-18-9

Product 1

HCID 67131297HCID 67131297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline] 1ad (4.5 g, 15.4 mmol) in dry CH2Cl2 (35 mL) was added NaHCO3 (6.47 g, 77 mmol) at room temperature. Then acetyl chloride (1.2 g, 15.4 mmol) was added dropwise at ambient temperature. The mixture was stirred for 2 hours at room temperature. After filtration, the filtrate was washed with brine, dried over Na2SO4 and evaporated under reduced pressure to give a white solid, which was washed with ether and filtered to afford the pure product 1-(1-benzyl-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1′-yl)ethanone 1ae (not shown). The solid (5.2 g, 15.6 mmol) was dissolved in MeOH (50 mL), then Pd(OH)2/C (0.25 g) was added under Ar. The suspension was hydrogenated under H2 (50 psi) at 50-55° C. overnight. After cooling and filtration, the filtrate was evaporated under reduced pressure to give 1-(2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1′-yl)ethanone 1ae (3.12 g, 83%, two steps). 1H NMR (CDCl3, 300 MHz) δ 7.46-7.49 (m, 2H), 7.21-7.26 (m, 3H), 3.82 (t, J=5.7 Hz, 2H), 3.38 (d, J=12.9 Hz, 2H), 3.08-3.16 (m, 2H), 2.38-2.48 (m, 2H), 2.24 (s, 3H), 1.97 (t, J=6.0 Hz, 2H), 1.77 (d, J=14.7 Hz, 2H). MS (ESI) m/z (M+H+) 245.2.

Workup

  1. filtrationAfter filtration
  2. washthe filtrate was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customto give a white solid, which
  6. washwas washed with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5da7c68cb42744e78bbb8c30e69737b2
Source dataset
uspto-grants-2012_09
Patent number
US08263605B2

Reaction notes

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