Hydrochloric Acid → HCID 22291229, compound

HRID 2076401Notes

Reaction equation

HRID 2076401 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:22][CH2:21][CH2:20][C:8]32[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]3)[CH:2]=1.[ClH:23]>ClCCl.Cl>[ClH:23].[ClH:23].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:8]3([CH2:9][CH2:10][NH:11][CH2:12]3)[CH2:20][CH2:21][CH2:22]2)[CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 222911941,1-Dimethylethyl 1-(3-pyridinyl)-1,7-diazaspiro[4.4]nonane-7-carboxylate

Product 1

HCID 22291229HCID 22291229, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 6-(3-pyridyl)-2,6-diazaspiro[4.4]nonane-2-carboxylate (100 mg, 0.330 mmol) in dichloromethane (5 mL) was rapidly stirred with 1 mL of 12 M hydrochloric acid at ambient temperature for 1 h, during which time the biphasic mixture became monophasic. The dichloromethane was evaporated, and the residue was dissolved in water (3 mL) and made strongly basic (pH 9) with potassium carbonate. The mixture was saturated with sodium chloride and extracted with chloroform (4×10 mL). The extracts were dried (K2CO3) and concentrated, first by rotary evaporation and then by high vacuum treatment. The viscous brown oil which resulted was 98% pure by GCMS and weighed 50 mg (73%). A sample of this free base (40 mg, 020 mmol) was dissolved in 10 drops of 12 M hydrochloric acid. The water was azeotropically removed by repeated treatment with small volumes of ethanol (˜5 mL) and rotary evaporation. The resulting solid was recrystallized from hot isopropanol to give 40 mg (72%) of fine tan crystals (mp 170-175° C.).

Workup

  1. customThe dichloromethane was evaporated
  2. dissolutionthe residue was dissolved in water (3 mL)
  3. extractionextracted with chloroform (4×10 mL)
  4. dry with materialThe extracts were dried (K2CO3)
  5. concentrationconcentrated, first by rotary evaporation
  6. customThe viscous brown oil which resulted
  7. customThe water was azeotropically removed
  8. customwith small volumes of ethanol (˜5 mL) and rotary evaporation
  9. customThe resulting solid was recrystallized from hot isopropanol

Sources & evidence

ORD record
ord-01c2aa30ba1c476d8ae042dad8067955
Source dataset
uspto-grants-2011_04
Patent number
US07923559B2

Reaction notes

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