Piperidine → HCID 178457775, compound

HRID 1181610Notes

Reaction equation

HRID 1181610 reaction equation
[C:1]([CH2:3][C:4]([N:6]([CH:17]([CH3:19])[CH3:18])[C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([SH:14])[S:13][C:9]=2[CH:8]=1)=[O:5])#[N:2].[CH:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)=O.N1CCCCC1>C(O)C>[C:1]([C:3]([C:4](=[O:5])[N:6]([CH:17]([CH3:19])[CH3:18])[C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([SH:14])[S:13][C:9]=2[CH:8]=1)=[CH:20][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)#[N:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 178457774HCID 178457774, compound

Product 1

HCID 178457775HCID 178457775, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

α-cyano-N-isopropyl-N-(2-mercaptobenzothiazol-6-yl)acetamide (99 mg, 0.339 mmol) and 4-formylbenzoic acid (56 mg, 0.374 mmol) were combined in absolute ethanol (1.4 ml). The mixture was stirred 15 minutes with activated 4A molecular sieves in a sealed vessel. Piperidine (67 μL, 0.678 mmol) was added and the mixture was heated to 80° C. After 1 hour, the solution was concentrated in vacuo and purified by preparative TLC (10% methanol, 90% dichloromethane) to yield 49 mg (34%). 1H NMR(CDCl3) δ1.17 (d, 6H), 4.93 (m, 1H), 7.16 (dd, 1H), 7.28 (dd, 1H), 7.32 (d, 1H), 7.69 (d, 2H), 7.93 (s, 1H), 7.98 (d, 2H); ESIMS: m/z 422 (M−H).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by preparative TLC (10% methanol, 90% dichloromethane)
  3. customto yield 49 mg (34%)

Sources & evidence

ORD record
ord-007dd33c9e14427696696701b27613fe
Source dataset
uspto-grants-2007_10
Patent number
US07285562B2

Reaction notes

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