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Sodium Bicarbonate → Phenylmethyl 4-[(6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)amino]-1-piperidinecarboxylate

HRID 656982
Notes
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Reaction equation

HRID 656982 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[N:18]1[C:23]2[O:24][CH2:25][CH2:26][O:27][C:22]=2[CH:21]=[C:20]([CH:28]=O)[N:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO>[N:18]1[C:23]2[O:24][CH2:25][CH2:26][O:27][C:22]=2[CH:21]=[C:20]([CH2:28][NH:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:6][CH2:7]2)[N:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178466404-Amino-1-N-Cbz-piperidineHCID 248916966,7-Dihydro-[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde

Product 1

HCID 68811936Phenylmethyl 4-[(6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)amino]-1-piperidinecarboxylateYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of phenylmethyl 4-amino-1-piperidinecarboxylate (for a synthesis see WO 2004/058144 Example 99(e)) (14.4 g crude, equivalent to 11 g, 47 mmol) and 6,7-dihydro[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde (for a preparation see Example 6(e)) (6.46 g, 39 mmol) in DCM (200 ml) and MeOH (10 ml) was stirred for 4 h at rt, then cooled in ice as sodium triacetoxyborohydride (12.4 g) was added over 15 min. After stirring for another 2 h, the mixture was treated with aqueous sodium bicarbonate to neutralise. The aqueous phase was extracted with DCM and the organic fractions were dried and evaporated. Chromatography on silica (750 g), eluting with 0-10% MeOH/DCM, gave the product (11.1 g, 62%).

Workup

  1. additionwas added over 15 min
  2. extractionThe aqueous phase was extracted with DCM
  3. customthe organic fractions were dried
  4. customevaporated
  5. washChromatography on silica (750 g), eluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-5f08df52828e4deab3b8adc4ece159ab
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071592B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes