Hydrochloric Acid → N-propyl-2,3-dihydro-1H-inden-2-amine

HRID 1596609Notes

Reaction equation

HRID 1596609 reaction equation
[C:1]([NH:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)(=O)[CH2:2][CH3:3].NC1C=C2C(=CC=1)CC(NC(=O)CC)C2.Cl>>[CH3:3][CH2:2][CH2:1][NH:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 107268885-Amino-2-propionamidoindanHCID 11701165Propanamide, N-(2,3-dihydro-1H-inden-2-yl)-

Product 1

HCID 17221237N-propyl-2,3-dihydro-1H-inden-2-amine

Procedure

2-Propionamidoindan (24, 0.83 g, 4.4 mmol) was converted to 28 (0.75 g, 98%), as described for the reduction of 25. A small amount was converted to the hydrochloride and recrystallized from 2-propanol, which yielded white crystals: mp 191-192° C.; 1H-NMR (CDCl3, 200 MHz) 1.04 (t, J=7.3, 3H), 1.70-1.82 (m, 2H), 3.01-3.20 (m, 4H), 3.29-3.48 (m, 2H), 4.00-4.11 (m, 1H), 7.18-7.30 (m, 4H); 13C NMR 9.7, 19.3, 35.5 (2C), 47.6, 58.0, 124.2 (2C), 127.0 (2C), 138.6 (2C). HRMS calcd. (obsd.) for C12H17N 175.1361 (175.1364).

Workup

  1. customrecrystallized from 2-propanol, which
  2. customyielded white crystals

Sources & evidence

ORD record
ord-8ca6ed7de2be4d3c9f611933f8d661d3
Source dataset
uspto-grants-2001_09
Patent number
US06291494B1

Reaction notes

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