1,2-Dichloroethane → Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-methylpiperidine-1-carboxylate

HRID 216048Notes

Reaction equation

HRID 216048 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.ClC(Cl)C.[CH3:36][N:37]([CH3:48])[C:38](=[O:47])[O:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([NH2:46])[CH:41]=1>>[CH3:36][N:37]([CH3:48])[C:38]([O:39][C:40]1[CH:41]=[C:42]([NH:46][C:14]([C:11]2([CH3:17])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])[CH:43]=[CH:44][CH:45]=1)=[O:47]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 63651,1-DichloroethaneHCID 298773-Aminophenyl dimethylcarbamateHCID 757711-HydroxybenzotriazoleHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid

Product 1

HCID 67037209Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-methylpiperidine-1-carboxylateYield 50%

Conditions

Temperature
85 °C

Procedure

1-(tert-Butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (67 mg, 0.28 mmol), EDC (64 mg, 0.33 mmol), HOBT (45 mg, 0.33 mmol) and dichloroethane (2.0 mL) were combined in a pressure rated sealed tube and stirred for 45 min. 3-Aminophenyl dimethylcarbamate (50 mg, 0.28 mmol) was added, and the mixture was heated at 85° C. for 18 hours. The mixture was concentrated and chromatographed (SiO2, 0-2% MeOH:CH2Cl2) to give the title compound in 50% yield. MS (ES+) [M+H]+=406.

Workup

  1. customrated sealed tube
  2. concentrationThe mixture was concentrated
  3. customchromatographed (SiO2, 0-2% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-cabc4fd5ff034804a10ac3b8ad7cbb03
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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