Water → N-[2-(4-Chlorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

HRID 2185913Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][NH:13][CH3:14])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[C:15]1([C:25](Cl)=[O:26])[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.O>C(Cl)Cl.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:9][CH2:10][OH:11])[CH2:12][N:13]([CH3:14])[C:25]([C:15]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)=[O:26])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred cooled (0° C.) mixture of 3-(4-chloropenyl)-N-methyl-4-amino-1-butanol (0.706 g, 3.30 mmol) in DCM (25 mL) and 1N NaOH (4.13 mL) was added dropwise a solution of 5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride (0.643 g, 3.30 mmol) in DCM (10 mL). The mixture was stirred at 0° C. for 2.5 h, H2O and DCM were added and the mixture was extracted with DCM (2×20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography (0%, 50%, 100% EtOAc in Et2O) provided the title compound (1.11 g, 90%) as a solid. MS m/z 372 (M+H).

Workup

temperatureTo a stirred cooled
extractionthe mixture was extracted with DCM (2×20 mL)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by chromatography (0%, 50%, 100% EtOAc in Et2O)

Sources & evidence

ORD record: ord-b41b220a3234487b93a072a95b1fe95f
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403601B1

Reaction notes

Loading…