Formaldehyde → 1-Acetamido-7-benzylmethylamino-5,6,7,8-tetrahydronaphthalene

HRID 863508Notes

Reaction equation

HRID 863508 reaction equation
[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C=O.[C:25]([BH3-])#N.[Na+]>C(O)(=O)C>[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([NH:15][CH2:16][CH2:17][C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:25]=3)[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 196961461-Acetamido-7-benzylamino-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 196962191-Acetamido-7-benzylmethylamino-5,6,7,8-tetrahydronaphthaleneYield 103.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-acetamido-7-benzylamino-5,6,7,8-tetrahydronaphthalene (14.3 g, 50 mmol), paraformaldehyde (15 g, 0.5 mol) and sodium cyanoborohydride (15.7 g, 0.25 mol) in acetic acid (250 mL) was stirred at room temperature for 48 h. The solvent was removed and the residue taken up in water:diethyl ether. The aqueous phase was basified with 12.5% NaOH and back extracted with ether. The combined ether layers were washed with saturated NaCl, dried over magnesium sulfate, filtered and evaporated to give a viscous syrup (16 g).

Workup

  1. customThe solvent was removed
  2. extractionback extracted with ether
  3. washThe combined ether layers were washed with saturated NaCl
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ca1851245f03440facd11e8bc3793770
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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