Isopropylamine → HCID 12800270, compound

HRID 2420174Notes

Reaction equation

HRID 2420174 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[OH-].[Na+].Cl[CH2:15][CH:16]1[O:18][CH2:17]1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>CC(C)=O.CO.O.C1C=CC=CC=1>[CH:19]([NH:22][CH2:15][CH:16]([OH:18])[CH2:17][O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:2](=[O:1])[CH2:3][CH2:4]2)([CH3:21])[CH3:20]

Participants

9

Procedure

To a mixture of 14.8 g. of 1-oxo-5-indanol, 8 g. of sodium hydroxide, and 100 ml. of water was added 50 ml. of 1-chloro-2,3-epoxypropane and after stirring vigorously the mixture for 16 hours at room temperature, 300 ml. of benzene and 100 ml. of water were added to the mixture. Then, the benzene layer fomred was recovered, washed twice each with 100 ml. of water, and then subjected to a distillation under reduced pressure to distill off benzene and then excessive 1-chloro-2,3-epoxypropane. The residue formed was mixed with 50 ml. of isopropylamine and 100 ml. of methanol and after stirring the mixture for 18 hours at room temperature, excessive isoporpylamine and methanol were distilled off under reduced pressure. Then, to the residue formed was added about 50 ml. of acetone and the mixture was allowed to stand overnight in a cold chamber to form crystals, which were recovered by filtration to provide 13.4 g. (yield 51%) of 3-isopropylamino-1-(1-oxo-5-indanyloxy)-2-propanol. By recrystallizing the product from acetone, the colorless crystals thereof melting at 100°-102° C. was obtained.

Workup

  1. additionTo a mixture of 14.8 g
  2. customThen, the benzene layer fomred was recovered
  3. washwashed twice each with 100 ml
  4. distillationof water, and then subjected to a distillation under reduced pressure
  5. distillationto distill off benzene
  6. customThe residue formed
  7. additionwas mixed with 50 ml
  8. distillationexcessive isoporpylamine and methanol were distilled off under reduced pressure
  9. customThen, to the residue formed
  10. additionwas added about 50 ml
  11. customto form crystals, which
  12. filtrationwere recovered by filtration
  13. customto provide 13.4 g

Sources & evidence

ORD record
ord-e2c7e971f38b45b48e76df34bbea27c1
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

Loading…