Triethylamine → N-[2-(4-chlorophenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

HRID 2185914Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:30][CH2:31][OH:32])[CH2:15][N:16]([CH3:29])[C:17]([C:19]2[C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH2:30][CH:31]=[O:32])[CH2:15][N:16]([CH3:29])[C:17]([C:19]2[C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred cooled (−78° C.) solution of oxalyl chloride (0.39 mL, 4.47 mmol) in DCM (10 mL) was added DMSO (0.64 mL, 9.00 mmol) in DCM (5 mL) dropwise. The solution was stirred at −78 ° C. for 5 min and a solution of N-[2-(4-chlorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide (1.11 g, 2.98 mmol) in DCM (6.0 mL) and DMSO (3.4 mL) was added dropwise. The solution was stirred at −78 ° C. for 15 min and triethylamine (2.50 mL, 17.9 mmol) was added. Stirring was continued at −78 ° C. for 30 min and then at room temperature for 2 h. 1N NCI (75 mL) and DCM (75 mL) were added, the layers separated, and the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography (silica gel; 50% Et2O/DCM) provided the title compound (1.10 g, 95%) as a tacky solid. MS rm/z 370 (M+H).

Workup

stirringThe solution was stirred at −78 ° C. for 15 min
stirringStirring
waitwas continued at −78 ° C. for 30 min
waitat room temperature for 2 h
customthe layers separated
dry with materialthe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by chromatography (silica gel; 50% Et2O/DCM)

Sources & evidence

ORD record: ord-808fcaf64a754b1a93f63c9a82bad1f3
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403601B1

Reaction notes

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