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

HRID 2413564Notes

Reaction equation

HRID 2413564 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 layers 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-222d3c013d264cc38e6cb45122acae5e
Source dataset
uspto-grants-1988_01
Patent number
US04719046

Reaction notes

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