Chloroacetaldehyde → 2-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 2085649Notes

Reaction equation

HRID 2085649 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].[Cl:23][CH2:24][CH:25]=O.Cl.C([BH3-])#N.[Na+]>CO>[Cl:22][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:25][CH2:24][Cl:23])=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]3)[CH2:20]1)[CH2:18]2)=[O:8]

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 227314875-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 114176532-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (7 g, Example 29b) and chloroacetaldehyde (50% solution in water, 6.6 ml) were stirred in methanol (120 ml) under nitrogen for 10 min. A mixture of 6M hydrochloric acid (1.8 ml) and methanol (1.8 ml) was added, followed by sodium cyanoborohydride (1.48 g). The mixture was stirred for 2.5 h. The methanol was then removed under reduced pressure and the residue partitioned between saturated aqueous sodium hydrogencarbonate and dichloromethane The aqueous layer was extracted twice more with dichloromethane and the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the sub-title compound (8.2 g).

Workup

  1. additionwas added
  2. customThe methanol was then removed under reduced pressure
  3. customthe residue partitioned between saturated aqueous sodium hydrogencarbonate and dichloromethane The aqueous layer
  4. extractionwas extracted twice more with dichloromethane
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4597dfe232b40f3beee887d4a6d3ac5
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

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