4-Butylbenzaldehyde → 7-(4-Butyl-phenylamino)-heptanoic Acid Methyl Ester

HRID 1699027Notes

Reaction equation

HRID 1699027 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8](C=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Cl.[CH3:14][O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23]>>[CH3:14][O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 709884-ButylbenzaldehydeHCID 13807349Methyl 7-aminoheptanoate hydrochloride

Product 1

HCID 543251847-(4-Butyl-phenylamino)-heptanoic Acid Methyl EsterYield 42.4%

Procedure

Following the procedure described in Step A of Example 68, reductive amination of 4-butyl-benzaldehyde (1.50 g, 9.26 mmol) with 7-aminoheptanoic methyl ester hydrochloride (1.51 g, 7.72 mmol) provided the title compound (955 mg). 1H NMR (300 MHz, CDCl3) δ7.29 (d, 2H), 7.16 (d, 2H), 3.85 (s, 2H), 3.67 (s, 3H), 3.54 (m, 1H), 2.70 (t, 2H), 2.59 (t, 2H), 2.29 (t, 2H), 1.60 (m, 6H), 1.32 (m, 6H), 0.92 (t, 3H); MS 306 (M+1).

Sources & evidence

ORD record
ord-4e7c5ed1cead40558adc360f9508062c
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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