Hydrochloric Acid → HCID 66581289, compound

HRID 2092671Notes

Reaction equation

HRID 2092671 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:25][CH2:24][C:14]3([CH2:23][CH2:22][C:17]4(OCC[O:18]4)[CH2:16][CH2:15]3)[C:13]2=[O:26])=[CH:8][CH:7]=1.Cl>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:25][CH2:24][C:14]3([CH2:15][CH2:16][C:17](=[O:18])[CH2:22][CH2:23]3)[C:13]2=[O:26])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66579660HCID 66579660, compound

Product 1

HCID 66581289HCID 66581289, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10-[4-(3-Methoxy-propyl)-phenyl]-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (460 mg, obtained in example 130, step 3) was dissolved in tetrahydrofuran (12 mL). Then hydrochloric acid (2M, 6.40 mL) was added dropwise over a period of 10 minutes and the mixture was stirred for 3 hours at RT. The reaction mixture was poured into ice/water and was extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a colorless solid (128 mg, 32%). MS (m/e): 316.2 [MH+].

Workup

  1. extractionwas extracted two times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-67b6224667ad449e969b368125af6243
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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