Hydrochloric Acid → HCID 89713965, compound

HRID 1518977Notes

Reaction equation

HRID 1518977 reaction equation
[CH:1]1([CH:4]([CH:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH3:5])[CH2:3][CH2:2]1.[CH2:12]([O:19][C:20](ON1C(=O)CCC1=O)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.ClCCl>[CH:1]1([CH:4]([CH:6]2[CH2:7][CH2:8][N:9]([C:20]([O:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:21])[CH2:10][CH2:11]2)[CH3:5])[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 83172Benzyl succinimido carbonateHCID 83905107HCID 83905107, compound

Product 1

HCID 89713965HCID 89713965, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve racemic 4-(1-cyclopropylethyl)-piperidine (1.75 g, 11.42 mmol) and N,N-dimethyl-4-pyridinamine (139.5 mg, 1.14 mmol) in pyridine (15 mL) and dichloromethane (30 mL). Add N-(benzyloxycarbonyloxy)succinimide (3.70 g, 14.84 mmol) and stir the solution for 4 hours. Pour the reaction mixture into 5N HCl and extract twice with EtOAc. Wash the organic extracts with sodium bicarbonate, followed by brine; dry over sodium sulfate; filter; collect the filtrate; and concentrate under reduced pressure. Purify the crude material on a silica gel flash column chromatography using a gradient of 0-20% EtOAc in hexane to give the title compound (3.0 g, 91%) as a clear oil. MS (m/z): 288 (M+1).

Workup

  1. extractionextract twice with EtOAc
  2. washWash the organic extracts with sodium bicarbonate
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. customcollect the filtrate
  6. concentrationand concentrate under reduced pressure
  7. customPurify the crude material on a silica gel flash column chromatography

Sources & evidence

ORD record
ord-93cbb2c1a9ec41b599d3c98bdb69b685
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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