Hydrochloric Acid → HCID 178484142, compound

HRID 1159380Notes

Reaction equation

HRID 1159380 reaction equation
Cl.[Cl:2][C:3]1[C:23]([CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:22]([Cl:30])[CH:21]=[CH:20][C:4]=1[O:5][C@H:6]1[CH2:9][C@H:8]([CH2:10][N:11](C)[C:12](=O)OC(C)(C)C)[CH2:7]1>O1CCOCC1>[Cl:2][C:3]1[C:23]([CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:22]([Cl:30])[CH:21]=[CH:20][C:4]=1[O:5][C@H:6]1[CH2:9][C@H:8]([CH2:10][NH:11][CH3:12])[CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178484145HCID 178484145, compound

Product 1

HCID 178484142HCID 178484142, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M HCl in dioxane (3.5 mL) was added to a solution of example 376, tert-Butyl ({trans-3-[2,4-dichloro-3-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl)methylcarbamate (1.65 g, 3.72 mmol) in 2 mL of dioxane. The mixture was stirred for 20 h and evaporated to dryness. Water (5 mL) was added to the residue, and the solution was subjected to extraction with CHCl3 (2×5 mL). The organic layers were discarded. Saturated K2CO3 (5 mL) was added to the water layer. The water solution was subjected to extraction with CHCl3 (3×10 mL). The combined extracts were dried with Na2SO4 and evaporated; the residue was dried in vacuo to give the title compound (850 mg, 67%) as a yellow oil. LC/MS data: 343.1, 344.1, 345.1 (M+H) (calculated for C17H24Cl2N2O 343.3). 1H NMR-data (DMSO-d6): 7.33 (d, 1H, J=9 Hz, Ar—H); 6.86 (d, 1H, J=9.0 Hz, Ar—H); 4.79-4.88 (m, 1H), 3.81 (s, 2H, CH2); 2.57 (d, 2H, J=7.3 Hz, CH2); 2.50-2.55 (m, 4H); 2.33-2.45 (m, 1H); 2.28 (s, 3H, NCH3); 2.21-2.27 (m, 2H); 2.10-2.19 (m, 2H); 1.60-1.68 (m, 4H).

Workup

  1. customevaporated to dryness
  2. additionWater (5 mL) was added to the residue
  3. extractionthe solution was subjected to extraction with CHCl3 (2×5 mL)
  4. additionSaturated K2CO3 (5 mL) was added to the water layer
  5. extractionThe water solution was subjected to extraction with CHCl3 (3×10 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated
  8. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-0af1adf41a154aa988a2dc4a76aca995
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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