Benzoyl chloride → HCID 89485790, compound

HRID 1469401Notes

Reaction equation

HRID 1469401 reaction equation
[OH:1][CH:2]([C:22]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[S:27][CH2:26][CH2:25][CH2:24][S:23]1)[CH:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][CH2:4]1.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:16]1([CH:6]2[CH2:5][CH2:4][CH:3]([CH:2]([O:1][C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:41])[C:22]3([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[S:27][CH2:26][CH2:25][CH2:24][S:23]3)[CH2:8][N:7]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 89485839HCID 89485839, compound

Product 1

HCID 89485790HCID 89485790, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of tert-butyl 5-{hydroxy[2-(pyridin-2-yl)-1,3-dithian-2-yl]methyl}-2-phenylpiperidine-1-carboxylate (0.71 g, 1.459 mmol), benzoyl chloride (0.41 g, 2.92 mmol), triethyl amine (0.51 mL, 3.65 mmol) and DMAP (8.91 mg, 0.073 mmol) in DCM (15 ml) was stirred at room temperature overnight. The mixture was diluted with DCM. The organic layer was washed with saturated KHSO4 and brine, and dried over MgSO4. The drying agent was filtered off and the filtrate was concentrated in vacuo to give the title compound. LC-MS m/e 591.13 [M+1]+.

Workup

  1. washThe organic layer was washed with saturated KHSO4 and brine
  2. dry with materialdried over MgSO4
  3. filtrationThe drying agent was filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e3a876c977744b2baa896f6aab10ba58
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Reaction notes

Loading…