Hydrochloric Acid → HCID 13375280, compound

HRID 1381766Notes

Reaction equation

HRID 1381766 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH:15]=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]([NH2:23])([CH2:21][OH:22])[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH3-]C#N.[Na+].CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.[ClH:70]>CCOCC.CCO.O.C1(C)C=CC=CC=1>[ClH:70].[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][NH:23][C:18]([CH3:17])([CH2:21][OH:22])[CH2:19][OH:20])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

11

Reactant 6

HCID 313Hydrochloric Acid2×HCID 15312-Amino-2-methyl-1,3-propanediolHCID 6101p-Toluenesulfonic acidHCID 6451Bromocresol GreenHCID 695049-AnthracenecarboxaldehydeHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 13375280HCID 13375280, compoundYield 40%

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent3×HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a 2 L Erlenmeyer flask was added 9-anthracenecarbaldehyde (Aldrich Chemical Co., Milwaukee, WI, 53201, 20.63 g, 0.1 mol) 2-methyl-2-amino-1,3-propanediol (Aldrich, 9.13 g, 86.8 mmol), p-toluenesulfonic acid.H2O (Eastman Kodak Co., Rochester, NY, 14650, 0.1 g, 0.5 mmol), and PhCH3 (500 mL). The mixture was warmed to reflux for a few minutes and H2O (2-3 mL) was driven off. The resulting golden colored solution was allowed to cool to RT, diluted with abs. EtOH (500 mL) and stirred overnight. NaBH3CN (Aldrich, 95%, 2.51 g, 42 mmol) was added to the reaction. After the NaBH3CN dissolved, an indicator (bromocresol green, Eastman, 5 mg) was added. To the resulting blue solution was added 5 drops of 1M solution of HCl gas in abs. EtOH every 15 minutes. After 3 days the indicator turned green then yellow and voluminous white precipitate was present in the flask. To the flask was then added 1M HCl gas (10 mL) in abs. EtOH. The reaction was diluted to 4 L with Et2O and stirred for 1 h. The precipitate was then collected by filtration through a medium porosity glass fritted funnel and pressed dry. The filter cake was washed with CH2Cl2 (4×500 mL), pressed and sucked dry, and dried (100°). The crude solid was recrystallized from EtOH/Et2O (3×) to give 13.44 g (40%) of 2-((9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride mp 139°-140° (dec), (C, H, Cl, N).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for a few minutes
  3. additiondiluted with abs
  4. customevery 15 minutes
  5. filtrationThe precipitate was then collected by filtration through a medium porosity glass fritted funnel
  6. custompressed dry
  7. washThe filter cake was washed with CH2Cl2 (4×500 mL)
  8. customsucked dry
  9. customdried (100°)
  10. customThe crude solid was recrystallized from EtOH/Et2O (3×)

Sources & evidence

ORD record
ord-a680601a463c41108846ec72de60670a
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

Loading…