3-(Diethylamino)-1-propanol → 3-(Diethylamino)propyl 1-phenylcyclobutanecarboxylate Hydrochloride

HRID 1955266Notes

Reaction equation

HRID 1955266 reaction equation
[C:1]1([C:7]2([C:11]([Cl:13])=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([N:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][OH:20])[CH3:15]>>[ClH:13].[C:1]1([C:7]2([C:11]([O:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:21][CH3:22])[CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 121593-(Diethylamino)-1-propanolHCID 232948921-Phenylcyclobutanecarbonyl chloride

Product 1

HCID 232949873-(Diethylamino)propyl 1-phenylcyclobutanecarboxylate Hydrochloride

Procedure

The title compound was prepared in an analogous manner to that in Example 36 by reacting 1-phenylcyclobutane-carbonyl chloride with 3-diethylaminopropanol at 80° C. for 5 h. The reaction mixture was filtered and chromatographed on silica gel using toluene-Et3N 95:5 as eluent. The yield was 0.8 g (45%); mp 108-111° C.; 1H NMR (D2O) δ 1.25 (t, 6H), 1.91-2.14 (m, 4H), 2.62 (m, 2H), 2.89 (m, 4H), 3.13 (q, 4H), 4.27 (t, 2H), 7.43 (m, 1H), 7.48 (m, 2H), 7.53 (m, 2H). Anal. (C18H27NO2.HCl) C, H, N.

Workup

  1. customat 80° C.
  2. customfor 5 h
  3. filtrationThe reaction mixture was filtered
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-920dcc0204084ae5847a328db0d9de9d
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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