1,2-Dichloroethane → HCID 178522831, compound

HRID 1050455Notes

Reaction equation

HRID 1050455 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>ClCCl.CO>[CH2:11]([NH:18][C:8]([C@H:5]1[CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:7][CH2:6]1)=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 181649HOAtHCID 178525779HCID 178525779, compound

Product 1

HCID 178522831HCID 178522831, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of cis-4-hydroxycyclohexanecarboxylic acid (1.0 g, 6.94 mmol), benzylamine (0.82 mL, 7.51 mmol) and HOAt (1.0 g, 7.35 mmol) in dichloromethane (50 mL) was added EDC free base (1.2 g, 7.73 mmol). The reaction was stirred overnight at room temperature, at which time it was washed with 1 N HCl, 1 N Na2CO3, brine, dried (MgSO4), filtered and concentrated under vacuum. Purification by silica gel chromatography (Analogix, SF25-80 g, 0 to 4% MeOH in CH2Cl2) gave (cis)-N -benzyl-4-hydroxycyclohexanecarboxamide (1.0 g, 4.29 mmol, 61.8% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.20 (t, J=5.81Hz, 1H), 7.26-7.38 (m, 2H), 7.11-7.27 (m, 3H), 4.31 (d, J=3.28 Hz, 1H), 4.25 (d, J=6.06 Hz, 2H), 3.76 (d, J=2.53 Hz, 1H), 2.08-2.22 (m, 1H), 1.73-1.89 (m, 2H), 1.56-1.69 (m, 2H), 1.33-1.49 (m, 4H). MS(ES) [M+H]+ 234.0.

Workup

  1. washwas washed with 1 N HCl, 1 N Na2CO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification by silica gel chromatography (Analogix

Sources & evidence

ORD record
ord-572538f561c94451bb724d3012048930
Source dataset
uspto-grants-2016_07
Patent number
US09382234B2

Reaction notes

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