Potassium Carbonate → HCID 22024264, compound

HRID 1792756Notes

Reaction equation

Br[C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:7][C:4]1[S:3][C:2]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)=[N:6][N:5]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 739534-Piperidineethanol

HCID 71719042-Bromo-5-methyl-1,3,4-thiadiazole

Product 1

HCID 22024264HCID 22024264, compoundYield 32.2%

Conditions

Temperature: 120 °C

Procedure

A suspension containing 2-bromo-5-methyl-1,3,4-thiadiazole (Modarai, B., et al. J. Heterocyclic Chem. (1974) 11, 343-5) (100 mg, 0.56 mmol), 4-piperidine ethanol (87 mg, 0.67 mmol) and potassium carbonate (77 mg, 0.56 mmol) was heated overnight at 120° C. The reaction was cooled and the mixture partitioned between water (10 ml) and ethyl acetate (30 ml), then the organic layer was washed with brine, dried (Na2SO4) and concentrated. Chromatography of the residue on silica gel (8 g; eluent 2.5% methanol/DCM) gave 1-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(2-hydroxyethyl)piperidine (41 mg, 32%), 1H nmr; 1.33 (m, 2H), 1.54 (q, 2H), 1.7 (m, 1H), 1.79 (m, 2H), 2.54 (s, 3H), 3.08 (m, 2H), 3.71 (t, 2H), 3.88 (m, 2).

Workup

temperatureThe reaction was cooled
customthe mixture partitioned between water (10 ml) and ethyl acetate (30 ml)
washthe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-c15051d52f544451954de1882d51f1db
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078403B1

Reaction notes

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