HCID 23045081, compound → HCID 14210580, compound

HRID 2108046Notes

Reaction equation

HRID 2108046 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:11][N:12](CC2C=CC=CC=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[OH:10])=[CH:4][C:3]=1[Cl:34]>[Pd]>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[OH:10])=[CH:4][C:3]=1[Cl:34]

Participants

3

Reactant 1

HCID 23045081HCID 23045081, compound

Product 1

HCID 14210580HCID 14210580, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

From 4-amino-3,5-dichloro-α-[[(phenylmethyl)[5-[2-(2-pyridinyl)ethoxy]pentyl]amino]methyl]benzenemethanol (2.67 g), using pre-reduced 10% palladium on charcoal (50% aqueous paste, 400 mg) as the catalyst for hydrogenation. FCC eluting with System C (95:5:1) gave the title compound as a pale yellow oil (1.74 g), t.l.c. (System C 95:5:1) Rf 0.07. A solution of the title compound (900 mg) in methanol (5 ml) was treated with fumaric acid (127 mg) in methanol (5 ml) and the solution was concentrated. Trituration of the resultant foam with diethyl ether gave the (E)-butenedioate (salt) (2:1) as a white solid (0.95 g), m.p. 140°-142°.

Workup

  1. washFCC eluting with System C (95:5:1)

Sources & evidence

ORD record
ord-357efea57c94496e936abd6730f06732
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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