Acetic Acid → 2-Propylamino-5-methoxytetralin

HRID 574294

Reaction equation

HRID 574294 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH2:8]2.C(O)(=O)C.[CH2:18]([NH2:21])[CH2:19][CH3:20].[BH3-]C#N.[Na+]>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([NH:21][CH2:18][CH2:19][CH3:20])[CH2:8]2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 7852PropylamineHCID 2591945-Methoxy-2-tetraloneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 102425482-Propylamino-5-methoxytetralinYield 62.1%

Procedure

This compound was prepared following Procedure A from 5-methoxy 2-tetralone (6.0 g, 34.0 mmol), acetic acid (5.1 ml, 102 mmol), propyl amine (5.5 ml, 68 mmol), and NaCNBH3 (5.3 g, 85 mmol) to give 4.63 g of 32b (62%, free base). 1H NMR (free base) (400 MHz, CDCl3) 0.92-0.964 (t, 3H, J=7.6 Hz), 1.39 (bs, 1H), 1.49-1.61 (m, 3H), 2.05-2.10 (m, 1H), 2.53-2.62 (m, 2H), 2.66-2.70 (t, 3H, J=7.6 Hz), 2.87-2.94 (m, 2H), 2.98-3.03 (m, 1H), 3.81 (s, 3H), 6.65-6.67 (d, 1H, J=8 Hz), 6.96-6.71 (d, 1H, J=8 Hz), 7.07-7.11 (t, 1H, J=7.2 Hz).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-07590c65ec564c238a2765edce39ca12
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Linked notes

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