Acetyl chloride → 2-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol diacetate

HRID 1193733Notes

Reaction equation

HRID 1193733 reaction equation
Cl.[CH:2]1[C:19]2[CH:18]=[CH:17][C:16]3[C:7](=[CH:8][C:9]([CH2:20][NH:21][C:22]([CH3:27])([CH2:25][OH:26])[CH2:23][OH:24])=[C:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[CH:11]4)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:28](Cl)(=[O:30])[CH3:29].C1C[O:35][CH2:34][CH2:33]1>>[C:28]([O:26][CH2:25][C:22]([NH:21][CH2:20][C:9]1[CH:8]=[C:7]2[C:16](=[C:15]3[C:10]=1[CH:11]=[CH:12][CH:13]=[CH:14]3)[CH:17]=[CH:18][C:19]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]2=1)([CH3:27])[CH2:23][O:24][C:34](=[O:35])[CH3:33])(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 133752782-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride

Product 1

HCID 155993182-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol diacetateYield 65.2%

Procedure

A mixture of 2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride (1B, 5.0 g, 13.1 mmol) and acetylchloride (Aldrich, 5.0 mL, 70.3 mmol) was refluxed in dry THF (200 mL) under N2 for 12 h. The reaction mixture was poured into a satd. NaHCO3 solution (500 mL) and extracted with EtOAc (3×500 mL). The EtOAc layes were combined, dried (K2CO3) and filtered to give a slightly yellow liquid. The solvent was removed to give an off-white solid. This was recrystallized 3× from PhCH3 /hexane (1:1). After filtration and drying, 3.67 g (65.2%) of 2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol diacetate was obtained mp 136°-137.5°, (C, H, N).

Workup

  1. additionThe reaction mixture was poured into a satd
  2. extractionNaHCO3 solution (500 mL) and extracted with EtOAc (3×500 mL)
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. customto give a slightly yellow liquid
  6. customThe solvent was removed
  7. customto give an off-white solid
  8. customThis was recrystallized 3× from PhCH3 /hexane (1:1)
  9. filtrationAfter filtration
  10. customdrying

Sources & evidence

ORD record
ord-a80572704fd04888b602d3e288924eee
Source dataset
uspto-grants-1989_03
Patent number
US04810727

Reaction notes

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