Hydrochloric Acid → HCID 69669934, compound

HRID 2038209Notes

Reaction equation

HRID 2038209 reaction equation
C(Cl)(C(Cl)=O)=O.[CH:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]1[N:17]1[C:21](=[O:22])[CH2:20][CH:19]([C:23]([OH:25])=O)[CH2:18]1)([CH3:9])[CH3:8].CCN(C(C)C)C(C)C.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.Cl>C(Cl)Cl.CN(C=O)C>[CH:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]1[N:17]1[CH2:18][CH:19]([C:23]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:25])[CH2:20][C:21]1=[O:22])([CH3:8])[CH3:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 69670118HCID 69670118, compound

Product 1

HCID 69669934HCID 69669934, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(COCl)2 (10 g, 79 mmol, 6.9 mL) and DMF (50 μL) were carefully added to 1-(2-isopropyl-5-methyl-cyclohexyl)-5-oxo-pyrrolidine-3-carboxylic acid (obtained as in EXAMPLE II, 10 g, 37.4 mmol) suspended in anhydrous CH2Cl2 (150 mL). The reaction mixture slowly turned into a homogeneous solution over about 3 hours, which was then concentrated in vacuo and dissolved in anhydrous CH2Cl2. The reaction mixture was subsequently added dropwise to a mixture of DIEA (9.7 g, 74.8 mmol) and piperidine (3.99 g, 56 mmol) at 0° C. with stirring. The reaction mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was poured into HCl (1 N) and extracted with CH2Cl2. The organic phases were collected, washed with brine, dried, and evaporated. Column chromatography with dichloromethane:methanol (95:5) provided 1-(2-isopropyl-5-methyl-cyclohexyl)-4-(piperidine-1-carbonyl)-pyrrolidin-2-one (10.8 g).

Workup

  1. concentrationwhich was then concentrated in vacuo
  2. dissolutiondissolved in anhydrous CH2Cl2
  3. stirringstirred for 3 hours
  4. extractionextracted with CH2Cl2
  5. customThe organic phases were collected
  6. washwashed with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-e48e3109aa0e49d98e16b0f7a4384e7e
Source dataset
uspto-grants-2013_11
Patent number
US08575349B2

Reaction notes

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