Hydrochloric Acid → HCID 178480925, compound

HRID 1852547Notes

Reaction equation

HRID 1852547 reaction equation
Cl.C(OC(=O)[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:25])[CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[CH2:11][CH2:10]1)(C)(C)C.CCOCC>CO>[NH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:15][C:16](=[O:25])[CH2:17][N:18]2[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178480926HCID 178480926, compound

Product 1

HCID 178480925HCID 178480925, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of HCl (2 M, 15 mL) was added to a solution of trans-{4-[2-(4-methyl-piperazin-1-yl)-acetylamino]-cyclohexyl}-carbamic acid tert-butyl ester (199 mg, 0.56 mmol) in MeOH (15 mL) at RT, and the resulting mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure to give a solid residue. Et2O was added to this material, and the resulting suspension was sonicated. The ether phase was decanted away, leaving a powdery brown solid which was purified by preparative TLC. The resulting oil was dissolved in the minimum quantity of MeOH, and Et2O was added. A solid precipitated; the liquid phase was decanted away to give, after drying, 75 mg of trans-N-(4-amino-cyclohexyl)-2-(4-methyl-piperazin-1-yl)-acetamide as a fine powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a solid residue
  3. customthe resulting suspension was sonicated
  4. customThe ether phase was decanted away
  5. customleaving a powdery brown solid which
  6. customwas purified by preparative TLC
  7. dissolutionThe resulting oil was dissolved in the minimum quantity of MeOH, and Et2O
  8. additionwas added
  9. customA solid precipitated
  10. customthe liquid phase was decanted away
  11. customto give
  12. customafter drying

Sources & evidence

ORD record
ord-9447c1ba99b44f1c87d452cbae8b3f1d
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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