Piperidin-4-ol → HCID 86584940, compound

HRID 2250740Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([C:13]2[N:14]=[C:15]([CH3:18])[S:16][CH:17]=2)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl.[OH:40][CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:29]([N:44]3[CH2:45][CH2:46][CH:41]([OH:40])[CH2:42][CH2:43]3)=[O:31])[S:11][C:7]=2[C:6]([C:13]2[N:14]=[C:15]([CH3:18])[S:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 0.070 g of 4-methoxy-7-(2-methyl-thiazol-4-yl)-benzothiazol-2-ylamine (0.00025 Mol) in THF (4 ml) at room temperature were added 0.054 ml N-ethyl-diisopropylamine (0.00031 Mol) and 0.001 g DMAP. 0.025 g of triphosgen (0.000085 Mol) were added and the whole mixture was heated to 70° C. for 1 hr. Then another 0.054 ml N-ethyl-diisopropylamine (0.00031 Mol) and 0.031 g of 4-hydroxy-piperidin (0.00031 Mol) were added and the reaction mixture was stirred at 70° C. for 1.5 hrs. Upon cooling to room temperature a precipitation formed, which was filtered and washed with THF. The filtrate was evaporated and the residue was subjected to column chromatography (silicagel, CH2Cl2/MeOH 9:1). The title product was obtained as a white solid (11%); F.p.: 145-150° C.

Workup

temperatureUpon cooling to room temperature
customa precipitation
customformed
filtrationwhich was filtered
washwashed with THF
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-276bb30fbc4c4a0c832d29f1f6262b59
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317007B2

Reaction notes

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