Thionyl Chloride → HCID 178471784, compound

HRID 505299Notes

Reaction equation

HRID 505299 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:7]([CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:19][CH2:18]1)[C:8]1[C:9]([CH2:14]O)=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:6]>C(Cl)Cl>[Cl:3][CH2:14][C:9]1[C:8]([N:7]([CH2:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:19][CH2:18]2)[CH2:5][CH3:6])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178471787HCID 178471787, compound

Product 1

HCID 178471784HCID 178471784, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (470 mg, 288 μL, 3-95 mmol) was added to a stirred solution of ethyl [trans-4-({ethyl[2-(hydroxymethyl)pyridin-3-yl]amino}methyl)cyclohexyl]acetate (132.2 mg, 0.395 mmol) in dry CH2Cl2 (10 mL) at room temperature. The reaction was stirred overnight at room temperature then quenched with pyridine (425 μL) and washed with water. The aqueous layer was extracted with CH2Cl2 (2×20 mL) an the combined extracts were dried (Na2SO4) and concentrated in vacuo to afford ethyl (trans-4-{[[2-(chloromethyl)pyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate. 1H NMR (500 MHz, CDCl3): δ 8.37 (dd, J=1.2, 4.5 Hz, 1 H); 7.51 (dd, J=1.4, 8.1 Hz, 1 H); 7.23 (dd, J 3.7, 8.3 Hz, 1 H); 4.86 (s, 2 H); 4.10 (q, J=7.1 Hz, 2 H); 3.03 (q, J=7.1 Hz, 2 H); 2.81 (d, J=7.1 Hz, 2 H); 2.14 (d, J=6.8 Hz, 2 H); 1.80-1.67 (m, 5 H); 1.42-1.29 (m, 1 H); 1.23 (t, J=7.1 Hz, 3 H); 0.99 (t, J=7.1 Hz, 3H); 0.94-0.86 (m, 4 H).

Workup

  1. customthen quenched with pyridine (425 μL)
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL) an the combined extracts
  4. dry with materialwere dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-625e964f40084b429bd93225c26e4e7f
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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