Thionyl Chloride → HCID 86590168, compound

HRID 276274Notes

Reaction equation

HRID 276274 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8]O)[CH:2]([CH3:4])[CH3:3].O=S(Cl)[Cl:12]>C1(C)C=CC=CC=1>[ClH:12].[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][Cl:12])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27720393-Isobutylamino-propan-1-ol

Product 1

HCID 86590168HCID 86590168, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-isobutyl-3-hydroxypropylamine (1.01 g, 7.70 mmol) in toluene (100 mL) was added SOCl2 (1.37 g, 11.6 mmol, 1.5 equiv.) and the resulting mixture was stirred at room temp. for 4 h. The resulting slurry was concentrated under reduced pressure to afford N-isobutyl-3-chloropropylamine HCl salt: 1H NMR (CDCl3) δ1.12 (s, 9H), 1.28 (t, J=7.0 Hz, 3H), 4.24 (q, J=7.0 Hz, 2H), 4.55 (s, 1H), 5.00 (s, 2H); 13C NMR (CDCl3) δ13.9, 27.8, 38.2, 61.5, 67.1, 67.3, 117.0, 167.1, 180.7; CI-LRMS m/z (rel abundance) 150 ((M+H)+, 100%).

Workup

  1. concentrationThe resulting slurry was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e1537a01b39344849f0a5f7d8ad46b74
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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