Benzoyl chloride → HCID 53757815, compound

HRID 1196258Notes

Reaction equation

HRID 1196258 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH:12]1[C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][CH2:19][CH2:18][C:13]21[O:17][CH2:16][CH2:15][O:14]2.C(N(CC)CC)C>ClCCl>[C:1]([NH:10][CH2:11][CH:12]1[C:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20][CH2:19][CH2:18][C:13]21[O:14][CH2:15][CH2:16][O:17]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 54370231HCID 54370231, compound

Product 1

HCID 53757815HCID 53757815, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzoyl chloride (7.7 g) in anhydrous dichloromethane (10 cc) is added dropwise, in the course of 40 minutes and while the temperature of the reaction mixture is maintained at +5° C., to a solution, cooled to +5° C., of (RS)-6-aminomethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (16.2 g) and triethylamine (5.6 g) in anhydrous dichloromethane (150 cc). The reaction mixture is then stirred for 4 hours at +25° C., thereafter washed with distilled water (125 cc) cooled to +5° C., dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized in a mixture (50 cc) of acetonitrile and isopropyl ether (50:50 by volume). The crystals are drained and dried. (RS)-6-Benzamidomethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (16 g) is obtained in the form of white crystals. M.p. 162° C.

Workup

  1. temperatureis maintained at +5° C., to a solution
  2. washwashed with distilled water (125 cc)
  3. temperaturecooled to +5° C.
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is recrystallized in a mixture (50 cc) of acetonitrile and isopropyl ether (50:50 by volume)
  8. customdried

Sources & evidence

ORD record
ord-b36329db01724cf7ad55c7c4dd93bedc
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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