Hydrochloric Acid → HCID 66783026, compound

HRID 1096232Notes

Reaction equation

HRID 1096232 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CO>C(Cl)Cl>[N:19]1([CH2:18][CH2:17][CH2:16][N:11]2[C:12](=[O:15])[CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 667834965-Oxo-4-(3-piperidin-1-yl-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 66783026HCID 66783026, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 7.3 g (21.50 mmol) of 5-oxo-4-(3-piperidin-1-yl-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester was in 140 ml CH2Cl2, cooled to 0° C. and treated with 54 ml (215 mmol) of HCl solution (4 M dioxane), then warmed to RT. After 3 h, 40 ml of MeOH were added to dissolve the precipitation and stirring was continued over night. The solution was evaporated, dissolved in aq. sat. NaHCO3. solution, the water evaporated and the solid extracted with in CH2Cl2:MeOH 9:1. Concentration afforded the title compound 5.0 g (97%) as yellow oil. MS: 240.1 (MH+).

Workup

  1. temperaturewarmed to RT
  2. dissolutionto dissolve
  3. customthe precipitation
  4. waitwas continued over night
  5. customThe solution was evaporated
  6. dissolutiondissolved in aq. sat. NaHCO3
  7. customsolution, the water evaporated
  8. extractionthe solid extracted with in CH2Cl2:MeOH 9:1
  9. concentrationConcentration

Sources & evidence

ORD record
ord-3ee64c0cb1ff41a1aab99d63ec7c51e4
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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