Ammonium Chloride → 4-{4-[(4-methylpiperazin-1-yl)methyl]tetrahydro-2H-pyran-4-yl}phenol

HRID 273003Notes

Reaction equation

C[S-].[Na+].C[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:25][N:22]1[CH2:21][CH2:20][N:19]([CH2:18][C:12]2([C:9]3[CH:8]=[CH:7][C:6]([OH:5])=[CH:11][CH:10]=3)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a suspension of sodium thiomethoxide (660 mg, 9.4 mmol) in N,N-dimethylformamide (2 ml) was added 1-{[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}4-methylpiperazine (410 mg, 1.3 mmol) in N,N-dimethylformamide (3 ml). The reaction mixture was heated to 130° C. under nitrogen for 18 hours. The mixture was then allowed to cool down to room temperature and saturated aqueous ammonium chloride was added. The mixture was extracted with ethyl acetate (2×30 ml). The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo to provide a pale brown oil. This was azeotroped with toluene and dried under high vacuum to provide the title compound (390 mg, 100%) as an off-white solid. HRMS ESI+ m/z 291.2062 [MH]+.

Workup

temperatureto cool down to room temperature
extractionThe mixture was extracted with ethyl acetate (2×30 ml)
dry with materialThe combined organic extracts were dried over sodium sulphate
filtrationfiltered
concentrationconcentrated in vacuo
customto provide a pale brown oil
customThis was azeotroped with toluene
customdried under high vacuum

Sources & evidence

ORD record: ord-5a2bdd95eef6439992dd03c805fd6110
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

Loading…