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Acetonitrile → 3-{3-[(7-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}heptyl)oxy]propyl}benzenesulfonamide

HRID 2118193
Notes
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Reaction equation

HRID 2118193 reaction equation
[CH2:1]([NH:8][CH2:9][C@@H:10]([C:12]1[CH:23]=[CH:22][C:15]2[O:16][C:17]([CH3:21])([CH3:20])[O:18][CH2:19][C:14]=2[CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]([S:42]([NH2:45])(=[O:44])=[O:43])[CH:39]=[CH:40][CH:41]=1.C(N(CC)C(C)C)(C)C.C(#N)C>O.C(OCC)C>[CH2:1]([N:8]([CH2:9][C@@H:10]([C:12]1[CH:23]=[CH:22][C:15]2[O:16][C:17]([CH3:20])([CH3:21])[O:18][CH2:19][C:14]=2[CH:13]=1)[OH:11])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]([S:42]([NH2:45])(=[O:44])=[O:43])[CH:39]=[CH:40][CH:41]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 115093953-{3-[(7-Bromoheptyl)oxy]propyl}benzenesulfonamideHCID 69196697(1R)-2-(benzylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Product 1

HCID 691987473-{3-[(7-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}heptyl)oxy]propyl}benzenesulfonamide
Yield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of (1R)-2-(benzylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (55.8 g), 3-{3-[(7-bromoheptyl)oxy]propyl}benzenesulfonamide (63.65 g), N,N-diisopropylethylamine (55 ml) and acetonitrile (200 ml) was stirred and heated under N2 at reflux for ca 21 h. The mixture was cooled to room temperature then diethyl ether (1000 ml) and water (500 ml) were added and the mixture stirred. The organic phase was washed with water (500 ml), then saturated brine (500 ml) and dried (Na2SO4). The solution was concentrated and the product purified by chromatography on flash silica gel (1000 g), eluting with petroleum ether:ethyl acetate (ratios ranging successively from 4:1 to 1:1) to give the title compound (97.7 g)-LC RT=1.54 min.

Workup

  1. temperatureheated under N2
  2. temperatureat reflux for ca 21 h
  3. stirringthe mixture stirred
  4. washThe organic phase was washed with water (500 ml)
  5. dry with materialsaturated brine (500 ml) and dried (Na2SO4)
  6. concentrationThe solution was concentrated
  7. customthe product purified by chromatography on flash silica gel (1000 g)
  8. washeluting with petroleum ether

Sources & evidence

ORD record
ord-2413a726f624489cbd9f10a6d58c75b2
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07442836B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes