(3-Bromopropyl)benzene → HCID 66932374, compound

HRID 518192Notes

Reaction equation

HRID 518192 reaction equation
BrC[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][O:12][C:13](=[O:39])/[CH:14]=[CH:15]/[C:16]1[CH:17]=[C:18]2[C:35](=[CH:36][CH:37]=1)[O:34][C:21]1([CH2:26][CH2:25][N:24]([C:27](OC(C)(C)C)=O)[CH2:23][CH2:22]1)[CH2:20][C:19]2=[O:38]>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:39])/[CH:14]=[CH:15]/[C:16]1[CH:17]=[C:18]2[C:35](=[CH:36][CH:37]=1)[O:34][C:21]1([CH2:26][CH2:25][N:24]([CH2:27][CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:23][CH2:22]1)[CH2:20][C:19]2=[O:38]

Participants

4

Reactant 2

HCID 12503(3-Bromopropyl)benzeneHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2×

Product 1

HCID 66932374HCID 66932374, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.185 ml, 1.33 mmol) and (3-bromopropyl)benzene (0.134 ml, 0.88 mmol) were added to a suspension of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester hydrochloride (150 mg, 0.44 mmol, Intermediate 1) in DCM (3 ml), and the mixture was stirred at RT for 24 h and then under reflux for 18 h. The solvent was removed and the crude mixture was purified by column chromatography (eluent: DCM/MeOH 97:3) to give (E)-3-{1′-(3-phenyl-propyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (173 mg) as a yellow oil.

Workup

  1. temperatureunder reflux for 18 h
  2. customThe solvent was removed
  3. customthe crude mixture was purified by column chromatography (eluent: DCM/MeOH 97:3)

Sources & evidence

ORD record
ord-f302e8f1e333438b94233c07fa857bf5
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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