2-Diisopropylaminoethanol → 2-(Diisopropylamino)ethyl 1-phenylcyclobutanecarboxylate Hydrochloride

HRID 1955267Notes

Reaction equation

HRID 1955267 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.[CH:14]([N:17]([CH:21]([CH3:23])[CH3:22])[CH2:18][CH2:19][OH:20])([CH3:16])[CH3:15]>>[ClH:13].[C:1]1([C:7]2([C:11]([O:20][CH2:19][CH2:18][N:17]([CH:21]([CH3:23])[CH3:22])[CH:14]([CH3:16])[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 73132-DiisopropylaminoethanolHCID 232948921-Phenylcyclobutanecarbonyl chloride

Product 1

HCID 232949762-(Diisopropylamino)ethyl 1-phenylcyclobutanecarboxylate Hydrochloride

Procedure

The title compound was prepared in an analogous manner to that in Example 36 by reacting 1-phenylcyclobutanecarbonyl chloride with 2-diisopropylaminoethanol at 80° C. for 17 h. The undissolved oil was separated from the reaction mixture and the toluene solution was chromatographed on silica gel using toluene-Et3N 98:2 as eluent. The yield was 1.5 g (77%); mp 110-114° C.; 1H NMR (D2O) δ 1.33 (d, 12H), 1.97 (m, 1H), 2.11 (m, 1H), 2.63 (m, 2H), 2.89 (m, 2H), 3.47 (t, 2H), 3.70 (m, 2H), 4.46 (t, 2H), 7.44 (m, 1H), 7.48 (m, 2H), 7.53 (m, 2H). Anal. (C19H29NO2 HCl) C, H, N.

Workup

  1. customat 80° C.
  2. customfor 17 h
  3. customThe undissolved oil was separated from the reaction mixture
  4. customthe toluene solution was chromatographed on silica gel

Sources & evidence

ORD record
ord-2d826cb483554cfab8dfc30a84cb6cd4
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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