4-(Piperazin-1-yl)benzene-1-sulfonamide → (S)-(-)-4-[4-[2-(Isochroman-1-yl)ethyl]homopiperazin-1-yl]benzenesulfonamide

HRID 368876

Reaction equation

HRID 368876 reaction equation
[CH:1]1([CH2:11][CH2:12]O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1.[N:14]1([C:21]2[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.N1(C2C=CC(S(N)(=O)=O)=CC=2)CCNCC1.ClCCC1C2C(=CC=CC=2)C(C)CO1.C1(C[C@H]2COC(=O)N2C(=O)C(C2C=CC=CC=2)C)C=CC=CC=1>>[C@H:1]1([CH2:11][CH2:12][N:17]2[CH2:18][CH2:19][CH2:20][N:14]([C:21]3[CH:22]=[CH:23][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:25][CH:26]=3)[CH2:15][CH2:16]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1

Participants

6

Reactant 5

HCID 9018974-(Piperazin-1-yl)benzene-1-sulfonamideHCID 14141298(-)-2-(Isochroman-1-yl)ethanolHCID 177928954-(Homopiperazin-1-yl)benzenesulfonamideHCID 232889381-(2-Chloroethyl)-4-methyl-isochromanHCID 56980759(4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

Product 1

HCID 53677310(S)-(-)-4-[4-[2-(Isochroman-1-yl)ethyl]homopiperazin-1-yl]benzenesulfonamide

Procedure

Following the general procedure for EXAMPLE 48 and making non-critical variations (-)-2-(isochroman-1-yl)ethanol (LXXIX) and 4-(homopiperazin-1-yl)benzenesulfonamide (IV; prepared from 4-fluorobenzenesulfonamide (III) and homopiperazine (II, Aldrich) by the method of EXAMPLE 47 Step 1) give the title compound, MS (m/z) 415; [α]D -50° (c 0.9996, methylene chloride); IR (mineral oil) 1153, 1595, 1102, 1511 and 1316 cm-1.

Sources & evidence

ORD record
ord-d0641541927a4557861986c670484f48
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Linked notes

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