1-Naphthalenemethanamine, alpha-methyl-, (alphaS)- → HCID 7394477, compound

HRID 1165389Notes

Reaction equation

HRID 1165389 reaction equation
[C:1]1([C@@H:11]([NH:13][C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]=[CH2:24])=[CH:17][CH:16]=2)[CH3:12])[C:10]2[C:5](=CC=CC=2)[CH:4]=[CH:3][CH:2]=1.C1([C@@H](N)C)C=CC=CC=1.C1([C@@H](N)C)C2C(=CC=CC=2)C=CC=1>>[C:1]1([C@@H:11]([NH:13][C:14](=[O:25])[C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]=[CH2:24])=[CH:19][CH:20]=2)[CH3:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:10]=1

Participants

4

Reactant 3

HCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 758181-Phenethylamine, (-)-HCID 18638022HCID 18638022, compound

Product 1

HCID 7394477HCID 7394477, compound

Procedure

The compound of this example [(S)-N-1-phenylethyl-4-allyloxybenzamide] was prepared in exactly the same manner as (S)-N-1-(1-naphthyl)ethyl-4-allyloxybenzamide in Example 1 except 2.5 g (0.014 mole) of (S)-1-phenylethylamine was used in Example 2 rather than 2 g (0.012 mole) of (S)-1-(1-naphthyl)ethylamine in Example 1. The (S)-N-1-phenylethyl-4-allyloxybenzamide product was isolated in a 67% yield; mp 147°-148° C.; [α]D25 -12.62° (c=0.745, CHCl3); IR (KBr): 3380 and 1640 cm-1 ; NMR (δ): 1.64 (3H, d, J=7.4 Hz), 4.60 (2H, d, J=4.4 Hz), 5.28-5.52 (3H, m), 5.88-6.60 (2H, m), 6.92 (2H, d, J=8.9 Hz), 7.16-7.44 (5H, m), 7.76 (2H, d, J=8.9 Hz). Anal. for C18H19NO2 ; Calcd: C, 76.87; H, 6.76; Found: C, 77.02; H, 6.82.

Sources & evidence

ORD record
ord-c5bb9987223e4c3bb9b5f8409758a5c5
Source dataset
uspto-grants-1990_03
Patent number
US04909935

Reaction notes

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