Dichloromethane → HCID 59830380, compound

HRID 1619734Notes

Reaction equation

HRID 1619734 reaction equation
Cl[C:2]1([CH:8]=[N:9][OH:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.[CH2:11]([N:18]1[CH2:22][CH2:21][C:20](=[CH2:23])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)Cl.C(N(CC)CC)C>O>[CH2:11]([N:18]1[CH2:22][CH2:21][C:20]2([O:10][N:9]=[C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:23]2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 11159600HCID 11159600, compoundHCID 86624330HCID 86624330, compound

Product 1

HCID 59830380HCID 59830380, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound C (3.9 g, 25.2 mmol, dissolved in abs. DCM (25 ml)) was added dropwise to a solution of 1-benzyl-3-methylenepyrrolidine (P) (2.18 g, 12.6 mmol) in abs. DCM (25 ml) at 0° C. within 10 min. A solution of triethylamine (14 ml, 10.2 g, 100.1 mmol) in abs. DCM (25 ml) was added to this mixture at 0° C. within 10 min. As the reaction was highly exothermic, cooling was carried out in an ice/sodium chloride mixture. The reaction mixture was stirred for 16 h at RT. For working up the mixture, DCM (50 ml) and water (70 ml) were added. The phases were separated. The aqueous solution was extracted with DCM (2×20 ml). The combined organic phases were washed successively with water (50 ml) and sat. NaCl solution (50 ml) and then dried and concentrated (5.3 g, yellow oil). The residue was purified by column chromatography [silica gel 60 (500 g); EtOAc/cyclohexane 1:2 (3 l)]. The desired compound Q was obtained as a solid in a yield of (2.4 g, 65%) having a melting point of 31-40° C.

Workup

  1. temperaturecooling
  2. additionwere added
  3. customThe phases were separated
  4. extractionThe aqueous solution was extracted with DCM (2×20 ml)
  5. washThe combined organic phases were washed successively with water (50 ml) and sat. NaCl solution (50 ml)
  6. customdried
  7. concentrationconcentrated (5.3 g, yellow oil)
  8. customThe residue was purified by column chromatography [silica gel 60 (500 g); EtOAc/cyclohexane 1:2 (3 l)]

Sources & evidence

ORD record
ord-c8673d2ac88d4c7682f49ca57bcbaf1a
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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