Benzene → HCID 19996126, compound

HRID 1086907Notes

Reaction equation

HRID 1086907 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:34])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:26]=[CH:25]OC=2C(N(CC)CC)=O)=[CH:4][C:3]=1[Cl:35].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:42]1[CH:47]=CC=CC=1>CCOCC>[NH2:1][C:2]1[C:3]([Cl:35])=[CH:4][C:5]([CH:9]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[O:34][C:9]([CH2:10][N:11]([CH2:47][CH3:42])[CH2:12][CH3:13])=[CH:25][CH:26]=2)[OH:34])=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 241BenzeneHCID 21226445Aluminium lithium hydrideHCID 86744915HCID 86744915, compound

Product 1

HCID 19996126HCID 19996126, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-[3-[[6-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]hexyl]oxy]propyl -N,N-diethyl-2-furancarboxamide (0.83 g) in benzene (6 ml) was added dropwise over 10 min to a stirred suspension of lithium aluminium hydride (175 mg) in dry ether (15 ml) under nitrogen. The mixture was stirred under nitrogen at 22° for 24 h, then quenched sequentially with water (1 ml), 2N sodium hydroxide solution (1 ml) and water (2 ml). The mixture was filtered through hyflo and the solids washed with toluene-ether (1:1, 10 ml). The combined filtrate and washings were dried and evaporated in vacuo to an oil. Purification by FCC eluting with System C (93:5:2) afforded the title compound as a pale yellow oil (0.59 g), t.l.c. (System A 39:10:1) Rf 0.5.

Workup

  1. customquenched sequentially with water (1 ml), 2N sodium hydroxide solution (1 ml) and water (2 ml)
  2. filtrationThe mixture was filtered through hyflo
  3. washthe solids washed with toluene-ether (1:1, 10 ml)
  4. customThe combined filtrate and washings were dried
  5. customevaporated in vacuo to an oil
  6. customPurification by FCC
  7. washeluting with System C (93:5:2)

Sources & evidence

ORD record
ord-1008dec3f46c4176986cf02f78bf477b
Source dataset
uspto-grants-1991_07
Patent number
US05032609

Reaction notes

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