Water → N-[2-(3,4-Difluorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

HRID 2185909Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][NH:14][CH3:15])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].[C:16]1([C:26](Cl)=[O:27])[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.O>C(Cl)Cl.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:12])[CH2:13][N:14]([CH3:15])[C:26]([C:16]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)=[O:27])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred cooled (0° C.) mixture of 3-(3,4-difluorophenyl)-N-methyl-4-amino-1-butanol (0.917 g, 4.26 mmol) in DCM (35 mL) and 1N NaOH (10 mL) was added dropwise a solution of 5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride (0.829 g, 4.26 mmol) in DCM (20 mL). The mixture was stirred at 0° C. for 2.5 h, additional 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 (1.25 g, 79%) as a solid. MS m/z 374 (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-976033e63fae491db24268a8c8b05808
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403601B1

Reaction notes

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