Benzylamine → HCID 19820422, compound

HRID 1030467Notes

Reaction equation

HRID 1030467 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28]Br>C1(C)C(C)=CC=CC=1>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]2[O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:27][CH2:28][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:10][CH2:11][O:12][C:13]=2[CH:18]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 19820417HCID 19820417, compound

Product 1

HCID 19820422HCID 19820422, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

9.1 ml of benzylamine were added to a solution of 7.26 g of 2-(2-bromoethoxy)-1-[2-(2-bromoethyl)phenoxy]-4-chlorobenzene in 714 ml of xylene and the mixture was heated to reflux for 24 h. After cooling the precipitate was removed with suction, washed with toluene and the filtrate was evaporated to dryness. The residue was chromatographed over silica with toluene-ethanol (9:1) to yield 4,17 g (64%) of 3-chloro-7,8,9,10-tetrahydro-8-phenylmethyl-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine. Rf 0.7 (silica; toluene-ethanol 8:2).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 h
  3. temperatureAfter cooling the precipitate
  4. customwas removed with suction
  5. washwashed with toluene
  6. customthe filtrate was evaporated to dryness
  7. customThe residue was chromatographed over silica with toluene-ethanol (9:1)

Sources & evidence

ORD record
ord-af035b54d8ba4d58883571c637142838
Source dataset
uspto-grants-1992_04
Patent number
US05106839

Reaction notes

Loading…