Carbodiimide → HCID 16678877, compound

HRID 551161Notes

Reaction equation

HRID 551161 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][C:9]([CH2:18][NH2:19])([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].N=C=N.[Cl:23][C:24]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:25]=1[C:26](O)=[O:27]>ClCCl>[Cl:23][C:24]1[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[CH:29][C:25]=1[C:26]([NH:19][CH2:18][C:9]1([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)[CH2:10][CH2:11][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:7][CH2:8]1)=[O:27]

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 111183632-chloro-4-(trifluoromethyl)benzoic AcidHCID 57931184HCID 57931184, compound

Product 1

HCID 16678877HCID 16678877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a large glass container with a sealable lid was placed 1-[1-(ethylsulfonyl)-4-(tetrahydrofuran-2-ylmethyl)piperidin-4-yl]methanamine (16, 3.4 g, 11.71 mmol), dichloromethane (50 ml) and PS-carbodiimide resin (35.1 mmol) along with 2-chloro-4-(trifluoromethyl)benzoic acid (3.41 g, 14.05 mmol). The lid was sealed and the bottle was shaken for 0.5 hours. The resin was filtered off and washed with EtOAc (3×25 ml) and the organics concentrated in vacuo to give an off-white solid. The residue was purified by column chromatography on silica gel, eluting with EtOAc/Hexanes to give 2-chloro-N-{[1-(ethylsulfonyl)-4-(tetrahydrofuran-2-ylmethyl)piperidin-4-yl]methyl}-4-(trifluoromethyl)benzamide (17) as a white solid. Calculated HRMS 497.1483 Found 497.1513. 1H NMR (300 MHz CDCl3): δ 7.70 (m, 2 H), 7.59 (d, J=7.8 Hz, 1 H), 3.86 (m, 3 H), 3.68 (q, J=5.7 Hz, 1 H), 3.57 (m, 2 H), 3.38 (m, 2 H), 3.16 (dt, J=10.2 Hz, 1 H), 2.99 (q, J=7.5 Hz, 2 H), 2.00 (m, 1 H), 1.85 (m, 2 H), 1.57 (m, 7 H), 1.38 (t, 7.8 Hz, 3 H.

Workup

  1. customThe lid was sealed
  2. filtrationThe resin was filtered off
  3. washwashed with EtOAc (3×25 ml)
  4. concentrationthe organics concentrated in vacuo
  5. customto give an off-white solid
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-340796f8fa384f1d8ac45c462fb1d121
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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