Acetyl chloride → cis-1-{4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanone

HRID 1809067Notes

Reaction equation

HRID 1809067 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.N1CC[O:27][CH2:26][CH2:25]1.C(Cl)(=O)C>C(Cl)Cl>[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:19][CH2:20][N:21]([C:26](=[O:27])[CH3:25])[CH2:22][CH2:23]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8083MorpholineHCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone

Product 1

HCID 86646703cis-1-{4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone [Enantiomer C] (CC-039) (0.150 g, 0.45 mmol) in DCM (2 mL) was added polymer supported morpholine (2.5 equivalents) and acetyl chloride (0.51 mmol). The reaction mixture was stirred for 3 hours, filtered and then the solvent evaporated. The product was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.095 g). LCMS m/z 375.27 [M+H]+ RT=9.71 min (Analytical Method 2).

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated
  3. customThe product was purified by HPLC
  4. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-41fbd67913ff42088274d2292e0de0b5
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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