Hydrochloric Acid → 3-hydroxy-3-[di-(2-hydroxy-2-phenylethyl)aminomethyl)-3,4-dihydro-2H-1,5-benzodioxepin hydrochloride

HRID 267796Notes

Reaction equation

HRID 267796 reaction equation
[OH:1][C:2]1([CH2:13][NH2:14])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1.[CH2:15]1[O:23][CH:16]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[ClH:24]>CO.CCOCC>[ClH:24].[OH:1][C:2]1([CH2:13][N:14]([CH2:15][CH:16]([OH:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:15][CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[OH:23])[CH2:3][O:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[O:7][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7276Styrene OxideHCID 155572973-(aminomethyl)-3,4-dihydro-2H-1,5-benzodioxepin-3-ol

Product 1

HCID 681470183-hydroxy-3-[di-(2-hydroxy-2-phenylethyl)aminomethyl)-3,4-dihydro-2H-1,5-benzodioxepin hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

3-Hydroxy-3-aminomethyl-3,4-dihydro-2H-1,5-benzodioxepin (2.30 g., 11.8 millimole) and styrene oxide (1.42 g., 11.8 millimole) are dissolved in methanol (12 ml.) and the solution then is stirred at ambient temperature for 48 hours. Evaporation of the reaction mixture gives 3.64 g. of a syrup which is chromatographed on a dry silica gel (150 g.) column which had been deactivated with about 25 ml. of water and packed in a 1 3/4 inches glass column. The first three fractions obtained upon elution with a 1:1 mixture of ether and chloroform are combined and dissolved in dry ether (50 ml.) and treated with a slight excess of ethanolic hydrogen chloride. The solid material is separated and dissolved in boiling ethanol (16 ml.) clarified with charcoal and filtered. The solvent was removed from the filtrate by evaporation yielding 3-hydroxy-3-[di-(2-hydroxy-2-phenylethyl)aminomethyl)-3,4-dihydro-2H-1,5-benzodioxepin hydrochloride, m.p. 221°-222° C. (dec.).

Workup

  1. customEvaporation of the reaction mixture
  2. customgives 3.64 g
  3. customof a syrup which is chromatographed on a dry silica gel (150 g.) column which
  4. customThe first three fractions obtained upon elution with a 1:1 mixture of ether and chloroform
  5. customThe solid material is separated
  6. dissolutiondissolved
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-33ebfb7bda494aa1a60d9ac849076bec
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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