Hexahydro-1,4-diazepine → (S)-(-)-4-[4-[2-(Isochroman-1-yl)ethyl]homopiperazin-1-yl]benzamide methanesulfonate

HRID 368877

Reaction equation

HRID 368877 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:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][CH:22]=2)[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.N1(C2C=C[C:39]([S:42](N)(=[O:44])=[O:43])=CC=2)CCNCC1.FC1C=CC(C(N)=[O:52])=CC=1.CNS(C1C=CC(F)=CC=1)(=O)=O.N1CCCNCC1.C1(C[C@H]2COC(=O)N2C(=O)C(C2C=CC=CC=2)C)C=CC=CC=1>>[CH3:39][S:42]([OH:44])(=[O:52])=[O:43].[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]([C:25]([NH2:27])=[O:26])=[CH:28][CH:29]=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

8

Reactant 7

HCID 68163Hexahydro-1,4-diazepineHCID 715724-FluorobenzamideHCID 9018974-(Piperazin-1-yl)benzene-1-sulfonamideHCID 24400544-fluoro-N-methylbenzene-1-sulfonamideHCID 14141298(-)-2-(Isochroman-1-yl)ethanolHCID 284109314-(Homopiperazin-1-yl)benzamideHCID 56980759(4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

Product 1

HCID 86753847(S)-(-)-4-[4-[2-(Isochroman-1-yl)ethyl]homopiperazin-1-yl]benzamide methanesulfonate

Procedure

Following the general procedure for EXAMPLE 49 and making non-critical variations (-)-2-(isochroman-1-yl)ethanol (LXXIX, 0.394 g) and 4-(homopiperazin-1-yl)benzamide (IV; 0.601 g prepared by the method of EXAMPLE 47, Step 1 from 4-fluorobenzamide, III, and homopiperazine, II) are combined to give the title compound, mp 163.75-165°; MS (m/z) 379; [α]D -41° (c, 0.975, DMF); IR (mineral oil) 1609, 1043, 1662, 1167 and 1216 cm-1.

Sources & evidence

ORD record
ord-041e872b461c43ec806a3accaba135d7
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Linked notes

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