Water → HCID 59656480, compound

HRID 561321Notes

Reaction equation

HRID 561321 reaction equation
C(OC(N1CCC(N)CC1)=O)(C)(C)C.[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:28][S:29]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35]([C:42]#[N:43])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-:44].[K+].[OH2:46]>>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:28][S:29]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35]([C:42]#[N:43])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:28][S:29]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35]([C:42]([OH:46])=[O:44])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 12682914-Amino-1-Boc-piperidineHCID 66998067HCID 66998067, compound

Product 2

HCID 59656480HCID 59656480, compoundHCID 66998067HCID 66998067, compound

Conditions

Temperature
100 °C

Procedure

4-Cyano-naphthalene-1-sulfonic acid (1-benzyl-piperidin-4-yl)-amide (33) was prepared according to the general procedure in Scheme 11, substituting 1-benzyl-piperidin-4-ylamine for 4-amino-piperidine-1-carboxylic acid tert-butyl ester. To a solution of 4-cyano-naphthalene-1-sulfonic acid (1-benzyl-piperidin-4-yl)-amide 33 (3.0 g, 7.43 mmol) in H2O (70 mL) was added KOH (4.2 g, 75 mmol). After stirring at 100° C. overnight, the resultant mixture became a clear solution. The aqueous layer was washed with CH2Cl2 twice and acidified to pH 4 by adding hydrochloric acid. After filtration, the resultant solid was dried to give 1.8 g of crude 4-(1-benzyl-piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid 34 in 57% yield. LCMS showed m/z: 425 (M+H)+. This material was used without further purification.

Workup

  1. washThe aqueous layer was washed with CH2Cl2 twice
  2. additionby adding hydrochloric acid
  3. filtrationAfter filtration
  4. customthe resultant solid was dried

Sources & evidence

ORD record
ord-f715a9f660cb4b31b42ba62bfcc8e2ff
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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