Triethylamine → Tert-butyl 1-(aminoimino-methyl)-piperidin-4-ylmethylcarbamate hemisulfite

HRID 963853

Reaction equation

HRID 963853 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.C([N:18]([CH2:21]C)CC)C.[C:23]([S:26]([OH:29])(=[O:28])=[O:27])([NH2:25])=[NH:24]>CN(C=O)C>[S:26]([OH:29])([OH:28])=[O:27].[NH2:24][N:18]=[CH:21][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3][CH2:2]1.[C:11]([O:10][C:9](=[O:15])[NH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([CH:23]=[N:25][NH2:18])[CH2:2][CH2:3]1)([CH3:12])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 9877361Methanesulfonic acid, aminoimino-

Product 1

HCID 131720709Tert-butyl 1-(aminoimino-methyl)-piperidin-4-ylmethylcarbamate hemisulfite

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 130 g of 1,1-dimethylethyl (4piperidinylmethyl)-carbamate in 1300 ml of DMF is treated with 138 ml of triethylamine and 61.8 g of formamidinesulfonic acid and the mixture is stirred at room temperature overnight. The precipitated material is filtered, suspended in 500 ml of ethanol, again filtered off and dried. There are obtained 65.6 g of tert-butyl 1-(aminoimino-methyl)-piperidin-4-ylmethylcarbamate hemisulfite, MS (ISP): 257.4 (M+H)+.

Workup

  1. filtrationThe precipitated material is filtered
  2. filtrationagain filtered off
  3. customdried

Sources & evidence

ORD record
ord-86e6069001dc41e4af4476953984ac18
Source dataset
uspto-grants-1998_06
Patent number
US05763604

Linked notes

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