4-Vinylbenzoic acid → HCID 70363320, compound

HRID 1165392Notes

Reaction equation

HRID 1165392 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[CH2:2].[CH3:12][C@@H:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OC1C=CC(C(O)=O)=CC=1)C=C.C1([C@@H](N)C)C2C(=CC=CC=2)C=CC=1>>[CH3:12][C@@H:13]([NH:20][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[CH2:2])=[CH:11][CH:10]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 140984-Vinylbenzoic acidHCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 4606904-(Prop-2-en-1-yloxy)benzoic acidHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 70363320HCID 70363320, compound

Procedure

(R)-N-α-Methylbenzyl-4-vinylbenzamide was prepared as above in Example 1 except 2.5 g (0.017 mole) of 4-vinylbenzoic acid and 2.13 g (0.018 mole) of (R)-α-methylbenzylamine (Aldrich) were used rather than the 2.0 g of 4-allyloxybenzoic acid and 2 g of (S)-1-(1-naphthyl)ethylamine in Example 1. The product was recrystallized from absolute ethanol to give 1.85 g (44%) of white crystals; mp 162°-163° C.; [α]D25 -25.49° (c=0.404, CHCl3); IR (KBr): 3390 and 1640 cm-1 ; NMR (δ): 1.64 (3H, d, J=7.4 Hz); 5.32 (1H, q, J=7.4 Hz); 5.44-5.94 (2H, m); 6.48-6.92 (2H, m), 7.24-7.82 (9H, m). Anal. for C17H17NO: Calcd: C, 81.27; H, 6.77. Found: C, 81.24; H, 6.79.

Workup

  1. customThe product was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-0c06f36a9e694ead8e29591a4bf8fe6a
Source dataset
uspto-grants-1990_03
Patent number
US04909935

Reaction notes

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